1-[(Phenyl)methyl]-2-methyl-5-[(2-phenyl-4-thiazolyl)methoxy]-1H-indole-3-acetic acid → 5-[(2-Phenyl-4-thiazolyl)methoxy]-1-(phenylmethyl)-2-methyl-1H-indole-3-ethanol

Participants

Reaction Steps

To a slurry containing lithium aluminum hydride (0.10 g, 2.6mmol) in tetrahydrofuran (40 mL), is added slowly at 23° C. a solution of the ester of Example 40 (1.0 g, 2.0 mmol) in tetrahydrofuran (10 mL). After stirring for 1 hour, the excess lithium aluminum hydride is quenched with ethyl acetate (5.0 mL), poured into saturated sodium chloride (200 mL) and extracted with ether (200 mL, 2×). The ether layer is washed with brine, dried over MgSO4, and concentrated to give crude product (0.8 g). Crystallization of the solid from ethyl acetate affords 0.5 g of title compound as a white solid in 55% yield, m.p. 114°-116° C.

Provenance & Evidence