Potassium Hydroxide → 2-(5-Chloro-2-fluorophenyl)ethan-1-ol

HRID 521483ノート

反応式

HRID 521483 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 27737235-Chloro-2-fluorophenylacetic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 670764502-(5-Chloro-2-fluorophenyl)ethan-1-ol収率 82.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 5 g (26.51 mmol) of 5-chloro-2-fluoro-phenylacetic acid in 60 ml of THF was added dropped to a suspension of 2.012 g (53.02 mmol) of lithium aluminium hydride in 26.5 ml of THF. 30 ml of THF were added, and the mixture was heated under reflux for 3 h. After cooling to 0° C., a solution of 929.7 mg (16.57 mmol) of potassium hydroxide in 4 ml of water was cautiously added and the mixture was stirred overnight at room temperature. The formed precipitate was filtered off with suction and washed with THF. The combined filtrates were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol 98:2) to give 3.8 g of the title compound.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. filtrationThe formed precipitate was filtered off with suction
  4. washwashed with THF
  5. dry with materialThe combined filtrates were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography (DCM/methanol 98:2)

出典と根拠

ORDレコード
ord-9e5fe564e2694887aa42288aa0107d58
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

反応ノート

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