tert-Butanol → HCID 14780564, compound

Participants

Reaction Steps

Dess-Martin periodinane (1.018 gm, 2.40 mmol) was dissolved in dry CH2Cl2 (12 ml), treated with t-butanol (178 mg, 2.40 mmol) and the resulting mixture was stirred at room temperature for 15 minutes. A solution of 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinemethanol (539 mg, 1.82 mmol) in CH2Cl2 (8 ml) was then added. After 25 minutes, the solution was then diluted with Et2O (40 ml) and 1N NaOH (25 ml), then stirred an additional 5 minutes. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with saturated NaHCO3 and brine, then dried (Na2SO4), filtered and stripped to give a yellow solid. Flash chromatography (Merck SiO2, 40% EtOAc in hexane) gave 4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde (491 mg, 92%) as a white solid. Analytically pure material was obtained by recrystallization from hot hexane.

Provenance & Evidence