tert-Butanol → HCID 21471506, compound

Participants

Reaction Steps

t-Butanol (175 mg, 2.35 mmol) was added to a stirring solution of Dess-Martin periodinane (1.005 gm, 2.37 mmol) in dry CH3CN (15 ml). After 15 minutes, a solution of 2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinemethanol (582 mg, 1.81 mmol) in CH3CN (9 ml) and CH2Cl2 (3 ml) was added to the mixture and stirring was continued for 40 minutes. The mixture was diluted with Et2O and quenched with 1N NaOH (25 ml). After 25 minutes of rapid mixing, the biphasic mixture was separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed in succession with 1N NaOH, H2O, and brine, then dried (Na2SO4), filtered and stripped to yield a solid residue. The residue was chromatographed (Merck SiO2, 30% hexane in CH2 Cl2) to give 2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde as a white solid (532 mg, 92%). An analytical sample was obtained by recrystallization from a minimum amount of hot hexane.

Provenance & Evidence