Diisobutylaluminumhydride → HCID 22163750, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of ethyl (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)propenoate (0.86 g) in dry tetrahydrofuran (25 ml) at 0° C. under an atmosphere of argon was treated dropwise with a solution of diisobutyl aluminium hydride in tetrahydrofuran (1M; 6.7 ml). The reaction mixture was stirred at 0° C. for 1 hour and then it was quenched by dropwise treatment with saturated aqueous sodium sulphate solution (25 ml). The resulting mixture was partitioned between water (100 ml) and diethyl ether (100 ml), and the organic layer was separated. The aqueous layer was extracted with diethyl ether (2×100 ml) and the combined organic layers were dried over magnesium sulphate and evaporated, to give (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)propen-1-ol (0.96 g), in the form of a yellow oil. [NMR (in a mixture of CDCl3 and D2O ): 1.54 (6H, d, J=7 Hz), 3.82 (1H, septet, J=7 Hz), 4.15 (2H, dd, J=7 Hz, 1 Hz), 5.55 (1H, dt, J=16 Hz, 7 Hz), 6.62 (1H, dt, J=16 Hz, 1 Hz), 7.21-7.32 (3H, m), 7.35-7.62 (6H, m), 8.23 (1H, s)].

Provenance & Evidence