Triacetoxyperiodinane → (2,4-Dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A flask containing Dess-Martin reagent (7.50 g, 17.7 mmol) in DCM (200 mL) was cooled to 0° C. and then a solution of (2,4-dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (3.00 g, 13.4 mmol, Intermediate 45, step a) in 100 mL of DCM was added. After 5 min, the ice bath was removed and the reaction was allowed to stir at room temperature for 45 min, at which time TLC (30% acetone-DCM) indicated the reaction was complete. The reaction was quenched with saturated NaHCO3 solution and about 2 mL of 1 N NaOH and the aqueous portion (pH˜9) was extracted with DCM (3×75 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give an amber oil. Flash chromatography on silica gel (10-40% EtOAc-DCM) afforded the title compound as a yellow solid.

Provenance & Evidence