Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)-1-fluoroethyl)benzaldehyde

HRID 471058

반응식

HRID 471058 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]([F:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>C1COCC1>[Si:11]([O:10][CH2:9][CH:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:26]=[O:27])[F:18])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 57989324(2-(3-Bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 579892013-(2-(tert-Butyldimethylsilyloxy)-1-fluoroethyl)benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of (2-(3-bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilane (example 39, step c) (1.8 g) in THF (36 mL) was cooled to −78° C. under an atmosphere of nitrogen and treated with butyllithium (1.8M in hexanes, 3.3 mL), added dropwise over 5 minutes. The solution was stirred at −78° C. for 30 minutes, treated with N,N-dimethylformamide (0.63 mL), stirred at −78° C. for a further 30 minutes, then removed from the cooling bath and allowed to warm to room temperature over 140 minutes. The solution was quenched by the addition of 10% aqueous ammonium chloride, and the resulting mixture was extracted twice with diethyl ether. The combined organic phases were washed with brine, dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 50% dichloromethane in isohexane to afford the subtitled compound as a colourless oil. Yield 1.26 g.

후처리

  1. additionadded dropwise over 5 minutes
  2. stirringstirred at −78° C. for a further 30 minutes
  3. customremoved from the cooling bath
  4. temperatureto warm to room temperature over 140 minutes
  5. customThe solution was quenched by the addition of 10% aqueous ammonium chloride
  6. extractionthe resulting mixture was extracted twice with diethyl ether
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous magnesium sulphate
  9. custompurified by flash chromatography on silica
  10. washeluted with 50% dichloromethane in isohexane

출처 및 근거

ORD 기록
ord-5570d5be608c4edbbfb8de116c0c13b8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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