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

HRID 1689397

反応式

HRID 1689397 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-495f26dc0f6d400596f1373aca5a746f
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

関連ノート

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