Dimethylformamide → trans-2-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl) acetonitrile

HRID 2202262ノート

反応式

HRID 2202262 の反応式
CS(O[CH2:6][C@@H:7]1[CH2:9][C@H:8]1[CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)=O.[C-]#N.[K+].[CH3:32][N:33](C=O)C>O>[Si:12]([O:11][CH2:10][C@@H:8]1[CH2:9][C@H:7]1[CH2:6][C:32]#[N:33])([C:25]([CH3:26])([CH3:27])[CH3:28])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 10025044trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate

生成物 1

HCID 131735738trans-2-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl) acetonitrile収率 94%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of trans-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate (1.23 g, 2.94 mmol), potassium cyanide (0.383 g, 5.88 mmol) and DMF (10 mL) was stirred overnight at 60° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10→60% ethyl acetate/hexane) to give trans-2-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)acetonitrile (0.970 g, 2.78 mmol, 94%) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10→60% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-7a7092ac1a1f423aa3bf29153142d695
出典データセット
uspto-grants-2016_06
特許番号
US09365520B2

反応ノート

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