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

HRID 2202262노트

반응식

HRID 2202262 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7a7092ac1a1f423aa3bf29153142d695
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365520B2

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