Organic Syntheses最新文献_第6页

A Convenient Method for the Removal of Tetrabutylammonium Salts from Desilylation Reactions 脱硅反应中四丁基铵盐脱除的一种简便方法

IF 0.7

Organic Syntheses Pub Date : 2022-01-01 DOI: 10.15227/orgsyn.099.0053

L. McDermott

{"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":"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":"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}

引用次数: 0

Discussion Addendum for: Asymmetric Michael Reaction of Aldehydes and Nitroalkenes 讨论附录:醛和硝基烃的不对称迈克尔反应

IF 0.7

Organic Syntheses Pub Date : 2022-01-01 DOI: 10.15227/orgsyn.099.0068

Y. Hayashi

引用次数: 0

Organocatalytic Dimerization of Succinaldehyde 琥珀醛的有机催化二聚反应

IF 0.7

Organic Syntheses Pub Date : 2022-01-01 DOI: 10.15227/orgsyn.099.0139

Steven H. Bennett

引用次数: 1

Preparation of MIDA Anhydride and Reaction with Boronic Acids. MIDA酸酐的制备及与硼酸的反应。

IF 0.7

Organic Syntheses Pub Date : 2022-01-01 DOI: 10.15227/orgsyn.099.0092

Peng-Jui Chen, Aidan M Kelly, Daniel J Blair, Martin D Burke

引用次数: 0

Synthesis of Triphenylene via the Palladium–Catalyzed Annulation of Benzyne 钯催化苯环化合成三苯

IF 0.7

Organic Syntheses Pub Date : 2022-01-01 DOI: 10.15227/orgsyn.099.0174

Katie A. Spence

引用次数: 0

Transformation of a N,N-Dimethylaniline N-oxide into a Tetrahydroquinoline Scaffold via a Formal Polonovski-Povarov Reaction N,N-二甲基苯胺N-氧化物转化为四氢喹啉支架的形式Polonovski-Povarov反应

IF 0.7

Organic Syntheses Pub Date : 2022-01-01 DOI: 10.15227/orgsyn.099.0381

Elizabeth L. Isaac

引用次数: 0

Synthesis of Chiral Aziridine Ligands for Asymmetric Alkylation with Alkylzincs: Diphenyl((S)-1-((S)-1-phenylethyl)aziridin-2-yl)methanol 二苯基((S)-1-((S)-1-苯乙基)叠氮吡啶-2-基)甲醇不对称烷基化手性配体的合成

IF 0.7

Organic Syntheses Pub Date : 2021-01-01 DOI: 10.15227/orgsyn.098.0446

Siyuan Sun

引用次数: 0

Large-Scale Preparation of Oppolzer’s Glycylsultam Oppolzer型甘磺坦的大规模制备

IF 0.7

Organic Syntheses Pub Date : 2021-01-01 DOI: 10.15227/orgsyn.098.0463

Upendra Rathnayake

引用次数: 0

Cu-catalyzed Allylic Perfluoroalkylation of Alkenes Using Perfluoro Acid Anhydrides: Preparation of N-(5,5,5-Trifluoro-2-penten-1-yl)phthalimide 用全氟酸酐催化烯丙基全氟烷基化:N-(5,5,5-三氟-2-戊烯-1-基)邻苯二胺的制备

IF 0.7

Organic Syntheses Pub Date : 2021-01-01 DOI: 10.15227/ORGSYN.098.0084

Yuma Aoki

引用次数: 3

C2 Amination of Pyridine with Primary Amines Mediated by Sodium Hydride in the Presence of Lithium Iodide 在碘化锂存在下氢化钠介导吡啶与伯胺的C2胺化反应

IF 0.7

Organic Syntheses Pub Date : 2021-01-01 DOI: 10.15227/ORGSYN.098.0363

J. Pang

{"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}

引用次数: 0