Trimethylsilyl cyanide → 8,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylacetonitrile

HRID 2389882노트

반응식

HRID 2389882 반응식
C[Si]([C:5]#[N:6])(C)C.[C:7]1([CH2:19]O)[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][CH2:18][C:12]=3[C:11]=12>ClCCl.C(=O)([O-])O.[Na+]>[C:7]1([CH2:19][C:5]#[N:6])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][CH2:18][C:12]=3[C:11]=12

참가 물질

5

반응물 2

HCID 82115Trimethylsilyl cyanideHCID 591793818,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol

생성물 1

HCID 591793778,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylacetonitrile수율 42%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of boron trifluoride diethyl ether complex (1.26 mL, 9.94 mmol) and trimethylsilyl cyanide (1.77 mL, 13.3 mmol) in dichloromethane (13 mL) was added a solution of 8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol (630 mg, 3.31 mmol) in dichloromethane (39 mL) under ice-cooling and an argon atmosphere, and the mixture was stirred at room temperature for 30 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (274 mg, yield 42%).

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

출처 및 근거

ORD 기록
ord-ce2c374aff41485a856250562bfee595
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273761B2

반응 노트

불러오는 중…