Lithium Hydroxide → Equol

Participants

Reaction Steps

To a mixture of alcohol of formula (9) (50 g) and triphenyl phosphine (151 g) in THF (2.5 L) diisopropyl azodicarboxylate (116.5 g) in THF (500 mL) was added at 15-20° C. and maintained at that temperature for 1-2 hours. About 5% lithium hydroxide solution (1000 mL) was added into the reaction mass and extracted with MTBE (3×750 mL) to remove the organic impurities. The pH of the aqueous layer was adjusted to 1-4 by dilute hydrochloric acid (250 mL). The reaction mass was maintained at RT for 5-6 hours and the product was filtered off. The crude product was taken with IPA (7.5 vol) and added water (22.5 vol). The reaction mass was then maintained at RT for 12-14 hours. The solid was filtered and dried at 50-55° C. for 10-12 hours to afford the title compound.

Provenance & Evidence