Potassium sodium tartarate → HCID 67690524, compound

Participants

Reaction Steps

To a stirred solution of 3-phenylmethylene-7-methoxycarbonylmethyl-2H-1-benzopyran-4-one (4.2 g, 14.3 mmole) in THF (70 ml) at 0° C. was added lithium aluminum hydride (2.16 g, 57.1 mmole) portionwise over 10 minutes. The mixture was slowly warmed to room temperature then heated at reflux for 5 hours. The mixture was cooled to 0° C. and 200 ml of saturated sodium-potassium tartrate solution was carefully added over 10 minutes. The mixture was stirred at room temperature overnight, the clear organic phase separated and the clear aqueous layer extracted with 2×100 ml of ether. The combined organic layers were washed with water and brine then dried over MgSO4. Filtration followed by evaporation in vacuo and chromatography (silica gel 2:1→1:5 hexane:ether) gave 2.61 of the title compound (64% yield).

Provenance & Evidence