Water → HCID 90202333, compound

Participants

Reaction Steps

To a solution of 3-(4-hydroxymethyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 19; 100 mg, 0.46 mmol) in DMSO (1.5 mL) was added Dess-Martin periodinane (214 mg, 0.5 mmol). The mixture was stirred at room temperature for 2.5 h. Water (5 mL) was added and the mixture was filtered to give a white solid. The filtrate was extracted three times with EtOAc and the combined extracts were dried (Na2SO4), filtered and evaporated to give a residue. The white solid from the first filtration was triturated with MeOH and the mixture was filtered. The filtrate was evaporated to give a second residue. The two residues were combined and purified by chromatography (25% acetone/CH2Cl2) to give 3-(4-formyl-phenyl)-isoxazole-5-carboxylic acid amide (50 mg, 50%).

Provenance & Evidence