Dimethyl Sulfoxide → 5-Oxo-1-phenylpyrrolidine-3-carboaldehyde

HRID 732668Notes

Reaction equation

HRID 732668 reaction equation
C(Cl)(=O)C(Cl)=O.ClCCl.CS(C)=O.[OH:14][CH2:15][CH:16]1[CH2:20][N:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:27])[CH2:17]1>C(N(CC)CC)C>[O:27]=[C:18]1[N:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:20][CH:16]([CH:15]=[O:14])[CH2:17]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 100127634-(Hydroxymethyl)-1-phenylpyrrolidin-2-one

Product 1

HCID 866285405-Oxo-1-phenylpyrrolidine-3-carboaldehyde

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Oxalyl chloride was added to a dichloromethane solution of DMSO at −78° C. and stirred for 20 minutes. Successively, this was mixed with a dichloromethane solution of 4-(hydroxymethyl)-1-phenylpyrrolidin-2-one and then with triethylamine 15 minutes thereafter, and stirred for 30 minutes. Thereafter, work-up and purification were carried out to obtain 5-oxo-1-phenylpyrrolidine-3-carboaldehyde. EN: 188.

Workup

  1. customThereafter, work-up and purification

Sources & evidence

ORD record
ord-35afcc8ddec64e3fb0987350007e77e2
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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