Pub Date : 2022-01-01DOI: 10.15227/orgsyn.099.0029
Nick Kilenyi
{"title":"Preparation of N-Formylamides by Oxidative Cleavage of N-Acylaminoacids","authors":"Nick Kilenyi","doi":"10.15227/orgsyn.099.0029","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0029","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341353","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 : 2022-01-01DOI: 10.15227/orgsyn.099.0068
Y. Hayashi
{"title":"Discussion Addendum for: Asymmetric Michael Reaction of Aldehydes and Nitroalkenes","authors":"Y. Hayashi","doi":"10.15227/orgsyn.099.0068","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0068","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341830","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 : 2022-01-01DOI: 10.15227/orgsyn.099.0053
L. McDermott
4-Bromophenol (2). A single-necked (24/40 joint) 250 mL round-bottomed flask is equipped with a Teflon-coated magnetic stir bar (3.0 x 1.5 cm, footballshaped). The apparatus is flame-dried under reduced pressure and cooled to 23 °C under an atmosphere of nitrogen. The flask is then equipped with a rubber septum and then placed under positive pressure of nitrogen using a nitrogen inlet. To the flask is then added (4-bromophenol)(tertbutyl)dimethylsilane (1) (4.5 g, 3.8 mL, 16 mmol, 1.0 equiv) (Note 2) via syringe. Then, dry THF (30 mL) (Note 3) is added at 23 °C to the flask via syringe and stirring is started (300 rpm). After one min of stirring, tetrabutylammonium fluoride solution (19 mL, 1.0 M in THF, 19 mmol, 1.2 equiv) (Note 4) is added via syringe dropwise over five min (Figure 1A). The reaction mixture is then allowed to stir (300 rpm) at 23 °C for 30 min (Note 5). Then, the rubber septum is removed, and calcium carbonate (8.2 g, 82 mmol, 5.3 equiv) (Note 6) is added in one portion followed by Dowex 50WX8, 200–400 mesh, ion exchange resin (24 g) (Note 7) in two equal portions using a funnel to assist with the addition. To the reaction mixture is then added methanol (60 mL) (Figure 1B) (Note 8), the rubber septum is Br OTBS i. TBAF, THF, 23 °C
4-溴酚(2)。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(3.0 x 1.5 cm，足球形)。该装置在减压下火焰干燥，并在氮气气氛下冷却至23°C。烧瓶装有橡胶隔膜，然后用氮气入口置于氮气正压下。然后通过注射器向烧瓶中加入(4-溴苯酚)(叔丁基)二甲基硅烷(1)(4.5 g, 3.8 mL, 16 mmol, 1.0当量)(注2)。然后，在23°C下通过注射器将干燥的THF (30ml)(注3)加入烧瓶中，并开始搅拌(300 rpm)。搅拌1分钟后，通过注射器滴入四丁基氟化铵溶液(19 mL, 1.0 M in THF, 19 mmol, 1.2 equiv)(注4)，持续5分钟(图1A)。然后将反应混合物在23°C下搅拌(300转/分)30分钟(注5)。然后，去除橡胶隔膜，将碳酸钙(8.2 g, 82 mmol, 5.3当量)(注6)加入一份，然后使用漏斗辅助添加Dowex 50WX8, 200-400目，离子交换树脂(24 g)(注7)，分两等份加入。然后在反应混合物中加入甲醇(60 mL)(图1B)(注8)，橡胶隔膜为Br OTBS i. TBAF, THF, 23°C
{"title":"A Convenient Method for the Removal of Tetrabutylammonium Salts from Desilylation Reactions","authors":"L. McDermott","doi":"10.15227/orgsyn.099.0053","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0053","url":null,"abstract":"4-Bromophenol (2). A single-necked (24/40 joint) 250 mL round-bottomed flask is equipped with a Teflon-coated magnetic stir bar (3.0 x 1.5 cm, footballshaped). The apparatus is flame-dried under reduced pressure and cooled to 23 °C under an atmosphere of nitrogen. The flask is then equipped with a rubber septum and then placed under positive pressure of nitrogen using a nitrogen inlet. To the flask is then added (4-bromophenol)(tertbutyl)dimethylsilane (1) (4.5 g, 3.8 mL, 16 mmol, 1.0 equiv) (Note 2) via syringe. Then, dry THF (30 mL) (Note 3) is added at 23 °C to the flask via syringe and stirring is started (300 rpm). After one min of stirring, tetrabutylammonium fluoride solution (19 mL, 1.0 M in THF, 19 mmol, 1.2 equiv) (Note 4) is added via syringe dropwise over five min (Figure 1A). The reaction mixture is then allowed to stir (300 rpm) at 23 °C for 30 min (Note 5). Then, the rubber septum is removed, and calcium carbonate (8.2 g, 82 mmol, 5.3 equiv) (Note 6) is added in one portion followed by Dowex 50WX8, 200–400 mesh, ion exchange resin (24 g) (Note 7) in two equal portions using a funnel to assist with the addition. To the reaction mixture is then added methanol (60 mL) (Figure 1B) (Note 8), the rubber septum is Br OTBS i. TBAF, THF, 23 °C","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341750","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 : 2022-01-01DOI: 10.15227/orgsyn.099.0139
Steven H. Bennett
{"title":"Organocatalytic Dimerization of Succinaldehyde","authors":"Steven H. Bennett","doi":"10.15227/orgsyn.099.0139","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0139","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341706","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 : 2022-01-01DOI: 10.15227/orgsyn.099.0092
Peng-Jui Chen, Aidan M Kelly, Daniel J Blair, Martin D Burke
A. MIDA Anhydride (1). A 500 mL single-necked, 24/40 round-bottomed flask equipped with a 5 x 2 cm Teflon-coated magnetic stirring bar is charged with methyliminodiacetic acid (40.0 g, 270 mmol, 1.00 equiv)(Notes 2 and 3), capped with a rubber septum and evacuated and backfilled with nitrogen via 20 G needle. Acetic anhydride (140 mL, 1.49 mol, 5.52 equiv) (Note 4) is added via syringe as a single portion to form a colorless suspension. This is immediately followed by the addition of pyridine (3.30 mL, 40.5 mmol, 0.15 eq.)(Note 5) in a single portion (Figure 1B). The flask is stirred under HO O N Me OH O
{"title":"Preparation of MIDA Anhydride and Reaction with Boronic Acids.","authors":"Peng-Jui Chen, Aidan M Kelly, Daniel J Blair, Martin D Burke","doi":"10.15227/orgsyn.099.0092","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0092","url":null,"abstract":"A. MIDA Anhydride (1). A 500 mL single-necked, 24/40 round-bottomed flask equipped with a 5 x 2 cm Teflon-coated magnetic stirring bar is charged with methyliminodiacetic acid (40.0 g, 270 mmol, 1.00 equiv)(Notes 2 and 3), capped with a rubber septum and evacuated and backfilled with nitrogen via 20 G needle. Acetic anhydride (140 mL, 1.49 mol, 5.52 equiv) (Note 4) is added via syringe as a single portion to form a colorless suspension. This is immediately followed by the addition of pyridine (3.30 mL, 40.5 mmol, 0.15 eq.)(Note 5) in a single portion (Figure 1B). The flask is stirred under HO O N Me OH O","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10428519/pdf/nihms-1920052.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10095845","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 : 2022-01-01DOI: 10.15227/orgsyn.099.0174
Katie A. Spence
{"title":"Synthesis of Triphenylene via the Palladium–Catalyzed Annulation of Benzyne","authors":"Katie A. Spence","doi":"10.15227/orgsyn.099.0174","DOIUrl":"https://doi.org/10.15227/orgsyn.099.0174","url":null,"abstract":"","PeriodicalId":19576,"journal":{"name":"Organic Syntheses","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"67341474","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 : 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":null,"pages":null},"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}
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