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

Participants

Reaction Conditions

Reaction Steps

Similar to the procedure described in J. Am. Chem. Soc. 1991, 7277, a flask containing Dess-Martin reagent (1.50 g, 3.54 mmol) in DCM (30 mL) was cooled to 0° C. and then a solution of (4-chlorophenyl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (500 mg, 2.24 mmol, Intermediate 42, step b) in 10 mL of DCM was added. After 5 min, the ice bath was removed and the mixture was allowed to stir at room temperature for 45 min, at which time TLC (20% EtOAc-DCM) indicated the reaction was complete. The mixture was quenched with a saturated NaHCO3 solution and 2 mL of 1 N NaOH 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 to give a light amber solid. Flash chromatography on silica gel (10% EtOAc-DCM) afforded the title compound as a white solid.

Provenance & Evidence