Acetic Anhydride → 1-Methylcyclobutyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methylcyclobutanol (6.2 g, 72.0 mmol) in DCM (50 mL) was added DMAP (0.440 g, 3.60 mmol) and TEA (15.05 mL, 108 mmol). Then, the mixture was cooled to 0° C. and acetic anhydride (13.46 mL, 108 mmol) was added and stirred at room temp for 24 h. The mixture was then washed with sat.NaHCO3 (100 mL), 1N HCl (100 mL), 10% NaOH (100 mL), brine (100 mL), dried (Na2SO4), filtered and concentrated to afford 1-methylcyclobutyl acetate (8 g, 62.4 mmol, 87% yield) as light yellow oil which was used in the next step as is without further purification. 1H NMR (500 MHz, CDCl3) δ 2.36-2.26 (m, 2H), 2.18-2.11 (m, 2H), 2.01-1.98 (m, 3H), 1.87-1.76 (m, 1H), 1.72-1.63 (m, 1H), 1.55 (s, 3H).

Provenance & Evidence