Hydrochloric Acid → HCID 86685802, compound

Participants

Reaction Steps

To a solution of (3R)-ethyl 2-(diphenylmethyleneamino)-3,7 dimethylnon-8-enoate (14.5 g, 37 mmol) in diethyl ether (25 mL) was added aqueous 1.5 N HCl solution (125 mL) and the reaction mass was stirred at room temperature overnight. The reaction mass was washed with diethyl ether (100 mL). The aqueous solution was basified using saturated sodium bicarbonate solution and extracted with ethyl acetate (100 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude compound (2.1 g, 23%). The crude compound was taken to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ ppm 5.85-5.60 (m, 1H), 4.98-4.85 (dd, J=1.6, 2.8 Hz, 2H), 4.10-4.06 (m, 2H), 3.15-3.14 (m, 1H), 2.15-2.02 (m, 1H), 1.94-1.75 (m, 3H), 1.32-1.17 (m, 9H), 0.95-0.93 (m, 3H), 0.84-0.74 (m, 3H). MS: MS m/z 227.7 (M++1).

Provenance & Evidence