4-Methyl-1,3-thiazole-2-carbaldehyde → 7586-99-4

Participants

Reaction Steps

To a solution of 4-methylthiazole-2-carbaldehyde of preparation 94 (5.8 g, 45.6 mmol) in anhydrous THF (100 mL) was added a THF solution of MeMgBr (3M, 30.4 mL, 91.3 mmol) drop-wise at −60° C. under N2, and the mixture was warmed to room temperature and stirred for another 2 hours. TLC (petroleum ether:EtOAc 2:1) showed the reaction was completed. The mixture was quenched by saturated NH4Cl solution (120 mL), and extracted with EtOAc (100 mL×3). The combined organic extracts were washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuum to give the residue which was purified by a silica gel column eluting with petroleum ether:EtOAc=20:1-8:1 to give the title compound as a yellow oil (3.4 g, 50%).

Provenance & Evidence