Acetone → 4-Ethoxy-but-2-ynoic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 4-ethoxy-but-2-yn-1-ol (1 g, 8.76 mmol) in acetone (26 mL) at 0° C. was added dropwise Jones reagent. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with methyl acetate. The organic layers were combined, dried (Na2SO4), and concentrated. The resulting 4-ethoxy-but-2-ynoic acid was methylated (TMSCHN2 (2 M), MeOH/toluene, room temperature, 3 hours) to afford 0.66 g of the title compound as a clear oil.

Provenance & Evidence