Water → 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one

HRID 964739노트

반응식

HRID 964739 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:14]CCCCC.IC.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:13])[CH:9]([CH:10]2[CH2:11][CH2:12]2)[CH3:14])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 8058HexaneHCID 134886181-(4-Chlorophenyl)-2-cyclopropylethan-1-one

생성물 1

HCID 134886191-(4-Chlorophenyl)-2-cyclopropylpropan-1-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
-30 °C

실험 절차

Crude 1-(4-chlorophenyl)-2-cyclopropylethanone (from the previous reaction) in dry dimethylformamide (150 ml) was added dropwise to a stirred suspension of hexane-washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen. After 1 hour the mixture was cooled to -30° C. and iodomethane (16.2 g, 114 mmol) in dry dimethylformamide (35 ml) added very slowly. The mixture was then poured into water and the resultant mixture extracted with ether. The extracts were washed with brine, dried and evaporated in vacuo. Chromatography [(SiO2, hexane-ethyl acetate (95:5)] gave 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one (7.66 g, approximately 70% pure, approximately 28% based on 1-(4-chlorophenyl)-2-cyclopropylethanol).

후처리

  1. washwashed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen
  2. extractionthe resultant mixture extracted with ether
  3. washThe extracts were washed with brine
  4. customdried
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-4b96c5b941cc4a74a9fd01d6c46e455a
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770741

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