Acetone, oxime → HCID 17952726, compound

Participants

Reaction Steps

Acetone oxime (172 mg, 2.35 mmol) was added to a solution of potassium t-butoxide (264 mg, 2.35 mmol) in 10 ml of THF. This was stirred for 30 min. at ambient temperature under a nitrogen atmosphere, then a solution of (5-bromo-2-fluoro-phenyl)-(2-ethoxy-3,5-diisopropyl-phenyl)-methanone (800 mg, 1.96 mmol) in THF was added. After 2 hrs., the reaction was quenched with saturated ammonium chloride solution (20 mL) and extracted with ether (2×20 mL). The organic layers were combined, dried over MgSO4 and evaporated. The residue was dissolved in ethanol (10 mL) and 1N HCl solution (10 mL) and refluxed for 1 h. The reaction mixture was portioned between ether and water after cooling to room temperature. The organic layer was dried over MgSO4 and evaporated. The residue was purified by silica gel column (10% ethyl acetate in hexanes) to give 5-bromo-3-(2-ethoxy-3,5-diisopropyl-phenyl)-benzo[d]isoxazole as a clear oil (313.2 mg, 40%).

Provenance & Evidence