Dimethyl Carbonate → Methyl 2-(2-methoxypyridin-4-yl)acetate

Participants

Reaction Steps

To the solution of lithium diisopropylamide (Aldrich, 2.0M, 122 mL, 244 mmol), THF (90 mL) and hexamethylphosphoric triamide (Aldrich, 16 mL, 89 mmol) at −78° C. under nitrogen was added, in 10 min, a solution of 2-methoxy-4-methylpyridine (10.0 g, 81 mmol) in THF (30 mL). After 30 min, a solution of dimethyl carbonate (Aldrich, 7.5 mL, 90 mmol) in THF (30 mL) was added over 15 min. The stirring was continued for 2 h at −78° C. before the reaction was quenched with MeOH (30 mL). The mixture was filtered through Celite and the cake was washed with EtOAc. The filtrate was concentrated in vacuo, and the crude product was purified by silica gel chromatography. MS: 182 (M+1).

Provenance & Evidence