Methanol → Methyl 2-hydroxy-2-(2-methyl-1,3-thiazol-4-yl)acetate

Participants

Reaction Steps

Acetyl chloride 725 μL, 10.2 mmol) was dropped at 0° C. in methanol (10 mL). After 30 minutes, a solution of 2-(2-methyl-1,3-thiazol-4-yl)-2-[(trimethylsilyl)oxy]acetonitrile (15a) (3.93 mmol) in methanol (30 mL) was added at 0° C. to the reaction. The mixture was then warmed at room temperature for 20 hours and concentrated under vacuum. A saturated aqueous solution of sodium bicarbonate (20 mL) was added to the residue and extracted with dichloromethane (2×20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 80/20) to afford the desired hydroxyl-ester (15b) as a yellow oil (560 mg, 2.99 mmol, 90%).

Provenance & Evidence