Dimethyl Sulfoxide → (2-Oxopyrrolidin-1-yl)acetaldehyde

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.87 mL, 10 mmol) was added dropwise to a solution of DMSO (0.71 mL, 10 mmol) in CH2Cl2 (7 mL) cooled to −78° C. After stirring 15 min at this temperature, 1-(2-hydroxyethyl)-2-pyrrolidinone (1 g, 7.7 mmol) was added dropwise. The mixture was stirred 30 min at −78° C. and Et3N (2.8 mL, 20 mmol) was added dropwise. After allowing the reaction to warm to rt, a solution of NaHCO3 was added and the mixture was extracted with CH2Cl2 (6×). The combined organic layers were dried and concentrated to give the product as an oil: 1H NMR (CDCl3) δ 9.60 (1H, s), 4.16 (2H, s), 3.46 (2H, t, J=7 Hz), 2.45 (2H, t, J=8 Hz), 2.11 (2H, m).

Provenance & Evidence