Methanol → Methyl 3-oxocyclobutane-1-carboxylate

Participants

Reaction Steps

A solution of N,N′-dicyclohexylcarbodiimide (7.17 g, 0.0347 mol) in methylene chloride (8 mL, 0.1 mol) was added dropwise to a stirred mixture of 3-oxocyclobutanecarboxylic acid (3.6 g, 0.032 mol), methanol (2.6 mL, 0.063 mol) and 4-dimethylaminopyridine (3.08 g, 0.0252 mol) in methylene chloride (20 mL, 0.2 mol). The mixture was stirred at rt for 24 h, then filtered through Celite. The filtrate was washed with 0.5 M HCl and sat. sodium bicarbonate, dried and concentrated to dry. The residue was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to give the desired ester (3.26 g, 80.64%). 1H NMR (CDCl3, 400 MHz): 3.78 (s, 3H), 3.43˜3.20 (5H, m) ppm.

Provenance & Evidence