HCID 23047463, compound → HCID 23047422, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of activated manganese dioxide (17.4 g), (E)-3-(3-isopropyl1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)propen-1-ol (2.14 g) and anhydrous diethyl ether (50 ml) was stirred at 20° C. under an atmosphere of argon for 17 hours. The suspension was then filtered and the filtrate was evaporated to give an orange-red oil. The oil was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v). The resulting crystalline solid was collected, washed with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v) and dried to give (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)propenal (1.8 g), in the form of a yellow solid, m.p. indistinct, approximately 170° C. [N.M.R. (in CDCl3): 1.6 (6H, d, J=7 Hz), 3.76 (1H, septet, J=7 Hz), 5.72 (1H, dd, J=8 Hz and 16 Hz), 6.75 (1H, d, J=8 Hz), 7.0-7.6 (9H, m), 7.15 (1H, d, J=16 Hz), 7.82 (1H, d, J=8 Hz), 9.43 (1H, d, J=8 Hz); Mass spectrum, m/e=340 (M+H+)]

Provenance & Evidence