Dimethyl Sulfide → 2,4-Dimethyl-1,3-thiazole-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A 3-neck 100 mL round-bottom flask was charged with anhydrous CH2Cl2 (20 mL) and oxalyl chloride (1.0 mL, 11.25 mmol) under N2 atmosphere. The mixture was cooled to −78° C. Anhydrous DMS O (1.1 mL, 15 mmol) was slowly added. The reaction was allowed to stir for 30 min. 2,4-dimethylthiazole-5-methanol (1.181 g, 7.5 mmol) in CH2Cl2 (5 mL) was slowly added. The reaction was allowed to stir for about 3 h, until TLC (1:1 EtOAc/Hexane) showed no starting material. The reaction was quenched with triethylamine (4.3 mL, 30 mmol) and stirred for 10 min. before warming to room temperature. The reaction was poured into Et2O (100 mL) and then extracted with water (2×25 mL). The organic phase was washed with NaHCO3(aq) (25 mL) and brine (25 mL). Dry over MgSO4 and concentrated under vacuum. The product was stored in the freezer. Yield: 1.04 g (89%) orange crystalline solid.

Provenance & Evidence