Dimethyl Sulfoxide → 2,2-Diphenyl-4-oxo-butyric acid methyl ester

HRID 424167

Reaction equation

HRID 424167 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH2:6]Br.C[N+]([O-:25])(C)C.CS(C)=O>>[CH3:1][O:2][C:3](=[O:20])[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[O:25]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1145Trimethylamine oxideHCID 22624494Methyl 4-bromo-2,2-diphenylbutyrate

Product 1

HCID 866311002,2-Diphenyl-4-oxo-butyric acid methyl ester

Procedure

A mixture of 4-bromo-2,2-diphenyl-butyric acid methyl ester (0.10 g, 0.300 mmol) and trimethylamine N-oxide (0.09 g, 1.2 mmol) in dimethyl sulfoxide (0.5 mL, 7 mmol) was stirred overnight at room temperature. The reaction was quenched with cold brine. The crude product was extracted three times with dichloromethane, dried over a bed of Na2SO4, filtered, and concentrated to dryness to provide crude title compound which was used without further purification.

Workup

  1. customThe reaction was quenched with cold brine
  2. extractionThe crude product was extracted three times with dichloromethane
  3. dry with materialdried over a bed of Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1c4bc66244d645269d180f2481cccfeb
Source dataset
uspto-grants-2012_01
Patent number
US08101791B2

Linked notes

Loading…