Water → Warfarin alcohol

Participants

Reaction Conditions

Reaction Steps

To a milky white suspension of 924 mg of commercially available warfarin in diethyl ether at 0° C. under an argon atmosphere is slowly added 125 mg of lithium aluminum hydride in portions. After 3 hours at 0° C. the reaction is warmed to room temperature. After 1 hour the mixture is re-cooled to 0° C. and slowly treated with 5 mL of water followed by 10 mL of 1N sodium hydroxide. After the bubbling ceases the layers are separated and the aqueous phase is washed with diethyl ether, acidified with 6 N hydrochloric acid, and repeatedly extracted with dichloromethane (methanol-chloroform co-solvents). The combined organic layers are dried (magnesium sulfate) and concentrated under reduced pressure. The residue is flash column chromatographed using 2% to 20% methanol in dichloromethane to afford 590 mg of a diastereomeric mixture of the title product as a white solid.

Provenance & Evidence