Aluminium lithium hydride → 4-(5-Bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol

Participants

Reaction Steps

To a suspension of 1.25 g (33 mmol) of lithium aluminum hydride in 50 nL of THF at 0° C. was added dropwise a solution of 11.7 g (27.5 mmol) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 20 mL of THF. The reaction was warmed to room temperature, stirred 2 hours, cooled to 0° C., carefully quenched with water, followed by 1N HCl, and extracted with EtOAc. The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo. The residue was triturated with hexanes and the solid collected by filtration to afford 7.6 g (72%) of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol.

Provenance & Evidence