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

HRID 507565ノート

反応式

HRID 507565 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-cff9995629294a48a42f2b0b8c9ad006
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

読み込み中…