Hexane → HCID 23166912, compound

Participants

Reaction Steps

A solution of methyl (E)-7-{1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]phthalazin-2-yl}-3,5-dihydroxyhept-6-enoate (3.16 g) in anhydrous diethyl ether (100 ml) was treated with activated manganese dioxide (12.61 g) and the mixture was stirred at room temperature under an argon atmosphere with the exclusion of light for 18 hours. The mixture was then filtered through diatomaceous earth. The filter pad was washed with diethyl ether (2×150 ml) and the combined filtrate and washings were concentrated to give an orange foam. This foam was subjected to flash chromatography on silica gel, using a mixture of diethyl ether and hexane (4:1 v/v) as eluant, to give methyl (E)-7-{1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]phthalazin-2-yl)-3-hydroxy-5-oxohept-6-enoate (1.61 g), in the form of an orange foam. [NMR (in CDCl3): 1.59 (6H, d, J=8 Hz), 2.55 (4 H, m), 3.45-4.15 (5 H, m), 4.40 (1H, m), 5.82 (1H, d, J=16 Hz), 7.05-7.70 (8H, m), 7.85 (1H, d, J=16 Hz), 8.30 (1H, s)].

Provenance & Evidence