Diisobutylaluminumhydride → 2-[2-Chloro-4-(trifluoromethoxy)phenoxy]ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[2-chloro-4(trifluoromethoxy)phenoxy]acetate (2.9 g, 10 mmol) was dissolved in dichloromethane (50 mL) and cooled to −78° C. A solution of diisobutylaluminum hydride in CH2Cl2 (1 M, 20 mL) was added and the reaction was warmed to 25° C. over 30 min. The reaction was quenched with methanol (2.0 mL) and poured into 0.5 N aqueous HCl. The aqueous phased was extracted with ethyl acetate and the combined organic layers were washed with brine and concetrated. The residue was chromatographed on silica gel eluting with 1:1 hexane:ethyl acetate gave 2-[2-chloro-4(trifluoromethoxy)phenoxy]ethanol.

Provenance & Evidence