Diethyl Ether → HCID 86718611, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde (1.0 g, 2.72 mmol) in THF (15 mL) at −78° C. under argon was added a 3 M solution of methyl magnesium bromide in diethyl ether (1.0 mL, 3.0 mmol). The reaction mixture was stirred at −78° C. for 10 minutes and then the solution poured onto brine cooled to 0° C. forming a gel. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic phase was separated, dried (Na2SO4), filtered, and the solvent removed under reduced pressure to give 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-ol (660 mg, 63% yield) as a tan oil.

Provenance & Evidence