Dimethyl Sulfoxide → 2-(3-Methoxyphenyl)cyclopentan-1-one

HRID 377306Notes

Reaction equation

HRID 377306 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][C:12]2=[O:11])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27596482-(3-Methoxyphenyl)-cyclopentanol

Product 1

HCID 123629382-(3-Methoxyphenyl)cyclopentan-1-oneYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of oxalic chloride (9.0 ml) in methylene chloride (200 ml) was added dimethyl sulfoxide (9.6 ml) at -78° C. After 10 minutes, to the solution was added a solution of 1-hydroxy-2-(3-methoxyphenyl)cyclopentane (13 g) in methylene chloride (20 ml) at the same temperature. After 15 minutes, to the mixture was added triethylamine at -78° C. and the mixture was warmed at 0° C. for 1 hour. The reaction mixture was washed with water and brine and dried over magnesium sulfate. The organic solution was concentrated and the residue was purified by column chromatography on silica gel to give 2-(3-methoxyphenyl)cyclopentanone (8.9 g).

Workup

  1. waitAfter 15 minutes
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic solution was concentrated
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-761c8943b06c4d2591ea631b3a32487e
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

Loading…