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

HRID 1074323Notes

Reaction equation

HRID 1074323 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-30 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4ed6d5b9b7d74b978b08937a67430ad7
Source dataset
uspto-grants-1990_11
Patent number
US04973767

Reaction notes

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