Hydrochloric Acid → HCID 18980008, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]-azepine (10 g), lithium chloride (12.5 g) and diisopropylamine (7.5 mL) in tetrahydrofuran (200 mL) was cooled to -70° C.; and butyllithium (2.5M in hexanes, 43 mL) was added, maintaining the temperature below -60° C. The mixture was warmed to 20° C. for 1 hour, and cooled to -70° C. A portion of the resulting 2,5-dihydro-2,5-dioxo-1,4-dilithio-3-methoxy-1H-benz[b]azepine solution (0.188M in tetrahydrofuran, 26 mL) was added to a solution of allyl bromide (0.85 mL) in tetrahydrofuran (15 mL) at -70° C. The mixture was warmed to room temperature, diluted with water, acidified (2N hydrochloric acid) and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and evaporated. The solid was purified by chromatography, with ethyl acetate:toluene (1:3) as the eluent, to give the title compound (0.189 g, 34%); NMR: 5.77 (m,1); 4.99 (d,1) 4.94 (s,1) 3.29 (d,2); MS: m/z=244(M+1).

Provenance & Evidence