Water → 2-(4-(2,2-Diethoxyethoxy)-2,3-difluorophenyl)ethanol

HRID 471168

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HRID 471168 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[C:13]([F:14])=[C:12]([CH2:15][CH2:16][OH:17])[CH:11]=[CH:10][C:9]=1[OH:18].Br[CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24].O>CN(C=O)C>[CH2:23]([O:22][CH:21]([O:25][CH2:26][CH3:27])[CH2:20][O:18][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][OH:17])=[C:13]([F:14])[C:8]=1[F:7])[CH3:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 534161452,3-Difluoro-4-(2-hydroxyethyl)phenol

생성물 1

HCID 579889892-(4-(2,2-Diethoxyethoxy)-2,3-difluorophenyl)ethanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

Cesium carbonate (0.99 g) was added to a solution of 2,3-difluoro-4-(2-hydroxyethyl)phenol (example 77, step b) (0.44 g) and 2-bromo-1,1-diethoxyethane (0.4 mL) in DMF (10 mL). The resulting suspension was heated at 90° C. for 18 h. The reaction was allowed to cool and poured into water (100 mL). The aqueous mixture was extracted with diethylether (3×100 mL). The combined organic solutions were washed with water (200 mL) and brine (200 mL), dried over magnesium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography eluting with isohexane to 1:1 ethyl acetate:isohexane gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 0.49 g.

후처리

  1. temperatureto cool
  2. extractionThe aqueous mixture was extracted with diethylether (3×100 mL)
  3. washThe combined organic solutions were washed with water (200 mL) and brine (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with isohexane to 1:1 ethyl acetate
  9. additionThe fractions containing product
  10. customevaporated

출처 및 근거

ORD 기록
ord-3468fecfd6244ff185c169c4e1177245
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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