Triacetoxyperiodinane → 1-(Dimethyl-1,3-thiazol-5-yl)-2-methylpropan-1-one

Participants

Reaction Conditions

Reaction Steps

A flask containing Dess-Martin reagent (2.5 g, 5.89 mmol) in DCM (50 mL) was cooled to 0° C. and then a solution of 1-(2,4-dimethylthiazol-5-yl)-2-methylpropan-1-ol (830 mg, 4.48 mmol, Intermediate 4: step a) in DCM (10 mL) was added. After 5 minutes, the ice bath was removed and the reaction mixture was allowed to stir at room temperature for 45 minutes. The mixture was quenched with saturated aqueous NaHCO3 and 1 N aqueous NaOH (2 mL) and the aqueous portion (pH˜9) was extracted with DCM (3×75 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (10% EtOAc-DCM) afforded the title compound as a colorless oil.

Provenance & Evidence