Pyridine → 1-Chloroethyl 2-methacryloyloxyethyl carbonate

Participants

Reaction Steps

Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of 1-chloroethyl chloroformate (1.20 ml, 11.00 mmol) and 2-hydroxyethyl methacrylate (1.22 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 1.76 g (74%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.85 (3H, d, J=6 Hz, CH3 --CH), 1.96 (3H,d, J=2 Hz, CH3 --C=), 5.55 (1H, m, CH=), 6.10 (1H, m, CH=), 6.38 (1H, k, J=6 Hz, CH--CH3).

Provenance & Evidence