Water → HCID 59370511, compound

Participants

Reaction Steps

To a solution (10 mL) of 4-fluoro-5-(hydroxymethyl)-2-(trifluoromethyl)benzonitrile (545 mg) and triethylamine (0.862 mL) in tetrahydrofuran was added dropwise methanesulfonyl chloride (0.289 mL) at 0° C. After the dropwise addition, the mixture was stirred at room temperature for 1.5 hr, water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (20 mL) and sodium borohydride (400 mg) was added thereto. The reaction mixture was stirred for 1.5 hr and methanol (2.5 mL) was added thereto. The mixture was stirred for 30 min, and saturated aqueous sodium hydrogencarbonate was added thereto. The mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=15:1→1:1) to give the title compound as a yellow oil (yield: 89 mg).

Provenance & Evidence