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

HRID 2094710노트

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HRID 2094710 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-95f9596218e84011a67e206950dcf308
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445530B2

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