Sodium borohydride → 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol

HRID 875255ノート

反応式

HRID 875255 の反応式
[Cl:1][CH2:2][C:3]([CH:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[O:6]1)=[O:4].[BH4-].[Na+]>C(O)C.O.ClCCl>[Cl:1][CH2:2][CH:3]([CH:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[O:6]1)[OH:4]

参加物

6

反応物 2

HCID 4311764Sodium borohydrideHCID 866579942-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone

生成物 1

HCID 672125072-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol収率 70%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone (0.33 g, 1.28 mmol, 88.4% A) in ethanol (2.5 ml) was cooled to 0° C. under nitrogen. NaBH4 (60.1 mg, 1.59 mmol) was added to the solution and the reaction mixture stirred for 2 hours. After checking by GPC that the starting product had disappeared, the mixture was diluted with demineralized water (7 ml) and dichloromethane (7 ml) and the phases separated. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to give crude 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol as a mixture of diastereoisomers 54:46 (0.30 g, 70% yield, 67.9% A).

後処理

  1. customthe phases separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-be09a0a66b9d45849aaa9811caf8eb00
出典データセット
uspto-grants-2015_03
特許番号
US08981127B2

反応ノート

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