Triacetoxyperiodinane → HCID 137328993, compound

Participants

Reaction Steps

A suspension of Dess-Martin periodinane (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 538 mg, 1.27 mmol) in methylene chloride (10 mL) was pipetted into a magnetically stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-dimethylamino-phenyl]-methanol (288 mg, 0.986 mmol) in methylene chloride (20 mL). The mixture was stirred for 15 min. Powdered sodium bicarbonate (˜500 mg) was added and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography, eluting with 10-40% ethyl acetate/hexanes, to give 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-dimethylamino-benzaldehyde (187 mg, 65%) as a yellow oil.

Provenance & Evidence