Tetrahydrofuran → Ethyl {4-[4,9-bis(ethyloxy)-1-hydroxy-3-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate

Participants

Reaction Conditions

Reaction Steps

Ethyl {4-[4,9-bis(ethyloxy)-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate (0.112 g, 0.24 mmol) was suspended in methanol (2 ml) and tetrahydrofuran (3 ml) added to dissolve the reactant. The reaction mixture was cooled to 0° C. in an ice bath and sodium borohydride (0.027 g, 0.72 mmol) added portionwise. Stirred under argon for 2-3 hours at 0° C. Further sodium borohydride was added to the reaction to push it to completion. The reaction mixture was evaporated to a solid and partitioned between EtOAc and ammonium chloride (saturated). The aqueous layer was extracted with EtOAc (×2) and the combined organics washed with brine and dried over MgSO4. Solvent was evaporated to give the title product as a gummy residue, which was triturated with hexane to afford a solid (0.111 g, 0.23 mmol).

Provenance & Evidence