Dimethyl Sulfoxide → 2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of anhydrous DMSO (3.41 mL, 48 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of oxalyl chloride (1.92 mL, 22 mmol) in CH2Cl2 (50 mL) at −60° C. To this mixture was added a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (2.48 mL, 20 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred for 15 min at −60° C. TEA (13.9 mL, 100 mmol) was added dropwise. The reaction mixture was then warmed to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added. The organic layer was separated and washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde that was used directly without further purification.

Provenance & Evidence