Sodium borohydride → HCID 58399574, compound

Participants

Reaction Steps

To a stirred solution of ethyl {4-[4,9-bis(ethyloxy)-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3,5-difluorophenyl}acetate (0.240 g, 0.50 mmol) in THF (10 ml) and methanol (5 ml) was added sodium borohydride (0.019 g, 0.50 mmol) slowly under an argon atmosphere. This was stirred at room temperature for 15 minutes, and then a further 0.057 g (1.50 mmol) of sodium borohydride was added to drive the reaction to completion. After 1.5 hours the reaction was evaporated and quenched with an aqueous solution of ammonium chloride. This was extracted ×2 with ethyl acetate (25 ml) and the combined extracts washed with brine. The organics layer was then dried over magnesium sulphate, filtered and evaporated to give the title compound as a yellow oily solid (0.240 g, 0.49 mmol) LC/MS: Rt=3.42 and 3.46, [MH]+ 486.

Provenance & Evidence