Potassium Hydroxide → 1-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one dimethyl acetal

HRID 1275216노트

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HRID 1275216 반응식
[OH-].[K+].[F:3][C:4]1[CH:5]=[C:6]([C:11](=[O:15])[CH:12]([OH:14])[CH3:13])[CH:7]=[CH:8][C:9]=1[F:10].[C:16](O)(=[O:18])C.[C:20](O)(=O)C.IC1C=CC=CC=1>CO>[CH3:20][O:15][C:11]([O:18][CH3:16])([C:6]1[CH:7]=[CH:8][C:9]([F:10])=[C:4]([F:3])[CH:5]=1)[CH:12]([OH:14])[CH3:13]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 12217721Iodo benzene diacetateHCID 229935141-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one

생성물 1

HCID 229934911-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one dimethyl acetal

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

In a round bottom flask containing 200 mL of MeOH was added pellets of potassium hydroxide (23.0 g, 410.0 mmol). The solution was cooled to 0° C. and 1-(3,4-difluorophenyl)-2-hydroxy-propan-1-one (7.0 g, 41.2 mmol) in 10 mL MeOH was added dropwise. The solution was stirred for 10 min and then iodobenzene diacetate (22.5 g, 70 mmol) was added in two portions. The solution first became orange and then turned yellow. It was stirred overnight at room temperature and then solvent was removed in vacuo. The residue was dissolved in water and was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine and then dried over Na2SO4. After filteration, the solvent was removed in vacuo to get 1-(3,4-difluorophenyl)-2-hydroxy-propan-1-one dimethyl acetal as a yellow viscous oil (crude wt.=9.2 g). It was dissoled in 150 mL of acetone and 10 drops of concentrated sulfuric acid were added. After stirring for 3 h, TLC analysis indicated that the reaction was complete. Acetone was removed in vacuo and after basification with saturated NaHCO3, the residue was extracted in EtOAc and was washed with brine. The organic layer was separated, dried over Na2SO4 and then filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (Rf=0.4, 3:2 hexane/EtOAc) to obtain 1-(3,4-difluorophenyl)-2-hydroxy-propan-1-one as a pale yellow oil (3.3 g, 51% yield over two steps).

후처리

  1. stirringIt was stirred overnight at room temperature
  2. customsolvent was removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionwas extracted with ethyl acetate (3×100 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter filteration, the solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-a656ccfa15ba4bdb8cec955be8a4d12c
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06159990

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