Pyridine → HCID 14552585, compound

Participants

Reaction Steps

To the above amine (0.86 g, 3.7 mmol) and pyridine (0.64 g, 8.0 mmol) in 8 ml of ether at 5° is added dropwise over 10 min. ethyl chloroformate (0.43 g, 4.0 mmol) in 2 ml of ether. The mixture is stirred at 5° for 1 hour and is then allowed to warm to RT. Excess ethyl chloroformate is quenched with water and the reaction mixture is poured into water and ether and the aqueous phase is extracted with ether (3×). The combined organic layers are washed with 2N ammonium sulfate, with 10% sodium carbonate, then with water until neutral and with brine. The organic layer is dried, filtered, the solvent removed and the product purified by prep. TLC to give ethyl N-{2-[4-(3-methyl-2-butenoxy)phenoxy]-1-methylethyl}carbamate m/s (M+) 307.

Provenance & Evidence