Dimethyl Sulfoxide → 1-(4-Chlorophenyl)-2-cyclopropylethan-1-one

HRID 1074321Notes

Reaction equation

HRID 1074321 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:23])[CH2:19][CH:20]2[CH2:22][CH2:21]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:23])[CH2:19][CH:20]2[CH2:21][CH2:22]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 190783841-(4-Chlorophenyl)-2-cyclopropylethanol

Product 1

HCID 134886181-(4-Chlorophenyl)-2-cyclopropylethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (5.5 ml, 63 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (5.5 ml, 78 mmol) in dry dichloromethane (150 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (5.00 g, 25.4 mmol) in dry dichloromethane (60 ml) was added to the mixture. After an hour triethylamine (27.5 ml, 197 mmol) was added, the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe extracts washed with water
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-51b3843b32364f849a6a32c5cfd6121c
Source dataset
uspto-grants-1990_11
Patent number
US04973767

Reaction notes

Loading…