Triacetoxyperiodinane → 3-(benzyloxy)cyclopentanone

Participants

Reaction Steps

To a solution of 3-(benzyloxy)cyclopentanol (530 mg) in dichloromethane (8 mL) is added at 0° C. 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-on (Dess-Martin periodinan, 8 mL of a 15% solution in dichloromethane). The mixture is stirred for 3 hours, diluted with dichloromethane, washed with 1 M aqueous NaOH solution and dried (MgSO4). The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→40:60) to give the title compound. Yield: 430 mg; LC (method 7): tR=0.90 min; Mass spectrum (ESI+): m/z=191 [M+H]+.

Provenance & Evidence