Pub Date : 2022-01-01DOI: 10.15227/orgsyn.099.0381
Elizabeth L. Isaac
{"title":"Transformation of a N,N-Dimethylaniline N-oxide into a Tetrahydroquinoline Scaffold via a Formal Polonovski-Povarov Reaction","authors":"Elizabeth L. Isaac","doi":"10.15227/orgsyn.099.0381","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0381","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"47 1 1","pages":""},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67342006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/orgsyn.098.0446
Siyuan Sun
{"title":"Synthesis of Chiral Aziridine Ligands for Asymmetric Alkylation with Alkylzincs: Diphenyl((S)-1-((S)-1-phenylethyl)aziridin-2-yl)methanol","authors":"Siyuan Sun","doi":"10.15227/orgsyn.098.0446","DOIUrl":"https://doi.org/10.15227/orgsyn.098.0446","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"1 1","pages":""},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67340853","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/ORGSYN.098.0363
J. Pang
N-Butylpyridin-2-amine (3). An oven-dried, 250 mL three-necked roundbottomed flask fitted with a 25 x 15 mm Teflon-coated oval magnetic stir bar, a thermometer, rubber septum and a Liebig reflux condenser, is connected to a Schlenk line (Note 2). Sodium hydride (NaH) (3.00 g, 75.0 mmol, 3.0 equiv) (Note 3) is charged to the reaction vessel, after which it is evacuated and backfilled with argon three times. Anhydrous THF (Note 4) (35 mL) is added via a syringe. The reaction flask is suspended in a 22 °C water bath, and lithium iodide (LiI) (6.69 g, 50.0 mmol, 2.0 equiv) (Note 5) is introduced through the top of the reflux condenser, after which the Ar line is reintroduced with an out needle in place for 5 min to exchange the atmosphere. The addition of LiI to the reaction mixture resulted in an exotherm which causes the internal temperature to rise to 35 °C. The reaction mixture is allowed to cool to 25 °C under Ar atmosphere while stirring (Note 6), at which time n-butylamine (2) (5.00 mL, 50.6 mmol, 2.0 equiv) (Note 7) is added to the grey suspension in one portion using a syringe. Pyridine (1) (1.985 g, 25.1 mmol, 1.0 equiv) (Note 8) is weighed into a dry N + H2N 2 (2 equiv) NaH (3 equiv) LiI (2 equiv)
{"title":"C2 Amination of Pyridine with Primary Amines Mediated by Sodium Hydride in the Presence of Lithium Iodide","authors":"J. Pang","doi":"10.15227/ORGSYN.098.0363","DOIUrl":"https://doi.org/10.15227/ORGSYN.098.0363","url":null,"abstract":"N-Butylpyridin-2-amine (3). An oven-dried, 250 mL three-necked roundbottomed flask fitted with a 25 x 15 mm Teflon-coated oval magnetic stir bar, a thermometer, rubber septum and a Liebig reflux condenser, is connected to a Schlenk line (Note 2). Sodium hydride (NaH) (3.00 g, 75.0 mmol, 3.0 equiv) (Note 3) is charged to the reaction vessel, after which it is evacuated and backfilled with argon three times. Anhydrous THF (Note 4) (35 mL) is added via a syringe. The reaction flask is suspended in a 22 °C water bath, and lithium iodide (LiI) (6.69 g, 50.0 mmol, 2.0 equiv) (Note 5) is introduced through the top of the reflux condenser, after which the Ar line is reintroduced with an out needle in place for 5 min to exchange the atmosphere. The addition of LiI to the reaction mixture resulted in an exotherm which causes the internal temperature to rise to 35 °C. The reaction mixture is allowed to cool to 25 °C under Ar atmosphere while stirring (Note 6), at which time n-butylamine (2) (5.00 mL, 50.6 mmol, 2.0 equiv) (Note 7) is added to the grey suspension in one portion using a syringe. Pyridine (1) (1.985 g, 25.1 mmol, 1.0 equiv) (Note 8) is weighed into a dry N + H2N 2 (2 equiv) NaH (3 equiv) LiI (2 equiv)","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"98 1","pages":"363-373"},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67340581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/ORGSYN.098.0263
Alexandra K. Bodnar
{"title":"Preparation of Hindered Aniline CyanH and Application in the Allyl-Ni-Catalyzed α,β-Dehydrogenation of Carbonyls","authors":"Alexandra K. Bodnar","doi":"10.15227/ORGSYN.098.0263","DOIUrl":"https://doi.org/10.15227/ORGSYN.098.0263","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"98 1","pages":"263-288"},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67340615","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/orgsyn.098.0194
Christian M Chaheine, Conner J Song, Paul T Gladen, Daniel Romo
A. Dimethyl 2-amino((4-methylphenyl)sulfonamido)malonate (2). To a single-necked, 500 mL round-bottomed flask containing a football-shaped, teflon-coated stir bar (5 cm) and fitted with a 24/40 glass, threaded gas-inlet adapter with a silicone/PTFE septa (Figure 1A) (Note 2), in-turn connected via chemically resistant tubing to a vacuum/nitrogen manifold is added commercially available dimethyl aminomalonate hydrochloride (1, 12.5 g, MeO2C CO2Me NH2 •HCl Ts2O, NEt3 THF, 0 to 23 °C MeO2C CO2Me NHTs
{"title":"Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(<i>S,E</i>)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.","authors":"Christian M Chaheine, Conner J Song, Paul T Gladen, Daniel Romo","doi":"10.15227/orgsyn.098.0194","DOIUrl":"https://doi.org/10.15227/orgsyn.098.0194","url":null,"abstract":"A. Dimethyl 2-amino((4-methylphenyl)sulfonamido)malonate (2). To a single-necked, 500 mL round-bottomed flask containing a football-shaped, teflon-coated stir bar (5 cm) and fitted with a 24/40 glass, threaded gas-inlet adapter with a silicone/PTFE septa (Figure 1A) (Note 2), in-turn connected via chemically resistant tubing to a vacuum/nitrogen manifold is added commercially available dimethyl aminomalonate hydrochloride (1, 12.5 g, MeO2C CO2Me NH2 •HCl Ts2O, NEt3 THF, 0 to 23 °C MeO2C CO2Me NHTs","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"98 ","pages":"194-226"},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9463714/pdf/nihms-1832364.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33459234","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/orgsyn.098.0242
Maciej Krzeszewski
{"title":"Synthesis of Tetraaryl-, Pentaaryl-, and Hexaaryl-1,4-dihydropyrrolo[3,2-b]pyrroles","authors":"Maciej Krzeszewski","doi":"10.15227/orgsyn.098.0242","DOIUrl":"https://doi.org/10.15227/orgsyn.098.0242","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"1 1","pages":""},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67339954","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/ORGSYN.098.0068
Milauni M Mehta
6-Acetylbenzothiophene (1). A single-necked (24/40 joint) 250 mL roundbottomed flask is equipped with a Teflon-coated magnetic stir bar (4.0 x 1.5 cm, football-shaped). The apparatus is flame-dried under vacuum, then cooled to 23 oC under an atmosphere of argon (Note 2). The flask is charged sequentially with 6-bromobenzothiophene (8.00 g, 37.5 mmol, 1 equiv) (Note 3), cesium fluoride (22.8 g, 150 mmol, 4 equiv) (Note 4), and tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol, 0.05 equiv) (Note 4) through the neck of the flask in singular portions. The neck of the flask is then fit with a rubber septum. An argon inlet needle and a purge needle are placed in the rubber septum, and the flask is purged for 5 min (Figure 1A). After 5 min, the vent needle is removed, and acetyltrimethylsilane (10.8 mL, 75 mmol, 2 equiv) (Note 5) is added in one portion over 1 min via a plastic syringe fit with an 18 G x 1.5’’ needle. 1,2-Dichloroethane (38 mL, 1 M) (Note 6) is then added to the flask via a plastic syringe fit with an 18 G x 6’’ needle in a single portion over 1 min (Figure 1B). The rubber septum is quickly removed and replaced with a Pd(PPh3)4 (5.0 mol%) CsF
6-乙酰苯并噻吩(1)。单颈(24/40关节)250毫升圆底烧瓶配备特氟龙涂层磁性搅拌棒(4.0 x 1.5 cm，足球形状)。该装置在真空下火焰干燥，然后在氩气中冷却至23℃(注2)。烧瓶通过烧瓶颈部按单份依次充入6-溴苯并噻吩(8.00 g, 37.5 mmol, 1当量)(注3)、氟化铯(22.8 g, 150 mmol, 4当量)(注4)和四(三苯基膦)钯(0)(2.17 g, 1.88 mmol, 0.05当量)(注4)。然后在烧瓶的颈部装上橡胶隔膜。在橡胶隔膜中放置氩气进口针和吹扫针，吹扫烧瓶5min(图1A)。5分钟后，取出排气针，通过18 G x 1.5“针的塑料注射器将乙酰三甲基硅烷(10.8 mL, 75 mmol, 2 equiv)(注5)在1分钟内加入一份。然后将1,2-二氯乙烷(38 mL, 1m)(注6)通过塑料注射器与18 G x 6“针配合，在1分钟内一次性添加到烧瓶中(图1B)。迅速取出橡胶隔膜，并用Pd(PPh3)4 (5.0 mol%) CsF代替
{"title":"Palladium-Catalyzed Acetylation of Arylbromides","authors":"Milauni M Mehta","doi":"10.15227/ORGSYN.098.0068","DOIUrl":"https://doi.org/10.15227/ORGSYN.098.0068","url":null,"abstract":"6-Acetylbenzothiophene (1). A single-necked (24/40 joint) 250 mL roundbottomed flask is equipped with a Teflon-coated magnetic stir bar (4.0 x 1.5 cm, football-shaped). The apparatus is flame-dried under vacuum, then cooled to 23 oC under an atmosphere of argon (Note 2). The flask is charged sequentially with 6-bromobenzothiophene (8.00 g, 37.5 mmol, 1 equiv) (Note 3), cesium fluoride (22.8 g, 150 mmol, 4 equiv) (Note 4), and tetrakis(triphenylphosphine)palladium(0) (2.17 g, 1.88 mmol, 0.05 equiv) (Note 4) through the neck of the flask in singular portions. The neck of the flask is then fit with a rubber septum. An argon inlet needle and a purge needle are placed in the rubber septum, and the flask is purged for 5 min (Figure 1A). After 5 min, the vent needle is removed, and acetyltrimethylsilane (10.8 mL, 75 mmol, 2 equiv) (Note 5) is added in one portion over 1 min via a plastic syringe fit with an 18 G x 1.5’’ needle. 1,2-Dichloroethane (38 mL, 1 M) (Note 6) is then added to the flask via a plastic syringe fit with an 18 G x 6’’ needle in a single portion over 1 min (Figure 1B). The rubber septum is quickly removed and replaced with a Pd(PPh3)4 (5.0 mol%) CsF","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"98 1","pages":"68-83"},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67340078","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2021-01-01DOI: 10.15227/ORGSYN.098.0147
E. Alwedi
{"title":"Synthesis of the Isocyanide Building Block Asmic, anisylsulfanylmethylisocyanide","authors":"E. Alwedi","doi":"10.15227/ORGSYN.098.0147","DOIUrl":"https://doi.org/10.15227/ORGSYN.098.0147","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":"13 1","pages":"147-170"},"PeriodicalIF":0.7,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67340321","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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