Ethyl Acetate → 1-(4-(Trifluoromethoxy)phenyl)cyclobutanecarbaldehyde

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Reaction Steps

To a solution of Example 31A (4.82 g, 0.02 mol) in dry dichloromethane (100 mL) at −78° C. under an argon atmosphere was added diisobutylaluminum hydride (24 mL, 1M solution in toluene). The reaction mixture was stirred at the same temperature for 1 hour and then quenched by dropwise addition of potassium sodium tartrate (10% solution in water). The resulting mixture was warmed to room temperature, stirred vigorously for 40 minutes and then diluted with dichloromethane. The organic phase was separated and the aqueous phase extracted with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography, eluted with 100% petroleum ether to petroleum ether: ethyl acetate=50:1 to 30:1) to give title compound as a viscous oil (2.7 g, yield 55.3%). LC-MS: m/z (M+H)+ 245.

Provenance & Evidence