Diisobutylaluminumhydride → HCID 86607634, compound

Participants

Reaction Steps

To a solution of 4-chloro-3-(2-fluoro-ethoxy)-benzoic acid 2-fluoro-ethyl ester (1.57 g, 5.93 mmol, 1.0 equiv) in anhydrous THF (30 mL) was added slowly over a time period of 15 min under cooling to −10° C. a solution of diisobutylaluminium hydride (17.8 mL, 17.80 mmol, 3.0 equiv; 1 M solution in toluene). After 1 h, the reaction mixture was poured on ice, extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with water (2×100 mL). The organic phase was dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with hexane/ethyl acetate (2:3) to give 1.19 g (98%) of the title compound.

Provenance & Evidence