Ammonium Chloride → (3-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)(4-fluorophenyl)methanol

HRID 2267341노트

반응식

HRID 2267341 반응식
C([Li])CCC.Br[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.[Cl-].[NH4+]>C1COCC1>[Si:15]([O:14][CH2:13][CH2:12][C:11]1[CH:10]=[CH:9][S:8][C:7]=1[CH:27]([C:26]1[CH:29]=[CH:30][C:23]([F:22])=[CH:24][CH:25]=1)[OH:28])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 680234-FluorobenzaldehydeHCID 60204457(2-(2-Bromothiophen-3-yl)ethoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 60204458(3-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)(4-fluorophenyl)methanol수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

n-Butyllithium in hexanes (12.7 mL, 1.6 M, 20.3 mmol) was added dropwise to a solution of (2-(2-bromothiophen-3-yl)ethoxy)(tert-butyl)dimethylsilane (5.9 g, 18.4 mmol) in anhydrous THF (15 mL) at −78° C. The resulting mixture was stirred at −78° C. for 30 min and 4-fluorobenzaldehyde (2.5 g, 20.3 mmol) in THF was added slowly. The mixture was stirred at −78° C. for 2 h and then warmed up to rt. After cooling again to 0° C. 50 mL of aqueous saturated ammonium chloride was added and the mixture was extracted with ethyl acetate (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo and the product was purified by flash chromatography eluting with ethyl acetate/hexane (1:3) to afford the title compound as a solid (3.8 g, 59%).

후처리

  1. stirringThe mixture was stirred at −78° C. for 2 h
  2. temperaturewarmed up to rt
  3. temperatureAfter cooling again to 0° C
  4. extractionthe mixture was extracted with ethyl acetate (3×80 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated in vacuo
  9. customthe product was purified by flash chromatography
  10. washeluting with ethyl acetate/hexane (1:3)

출처 및 근거

ORD 기록
ord-922aeeea72b54aa68cb735041201ddcd
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858785B2

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