Sodium hydride → HCID 178468918, compound

Participants

Reaction Steps

A solution of 5-(adamantan-1-yloxymethyl)-2-o-tolyl-2H-pyrazol-3-ol (160 mg, 0.47 mmol) in anhydrous THF (4 mL) was added to a suspension of sodium hydride (26 mg of 60% dispersion in oil, 0.65 mmol) in THF (2 mL) under a dry argon atmosphere at room temperature. The mixture was stirred for 30 min. and a solution of 3-ethoxycarbonylphenyl isocyanate (99 mg, 0.5 mmol) in THF (1 mL) added. Stirring was continued for 1 h and the mixture partitioned between 5% KHSO4 (40 mL) and EtOAc (40 mL). The organic phase was washed with brine (30 mL), and dried (MgSO4). Filtration and evaporation of the solvent afforded the product as a red solid, (250 mg, 100%).

Provenance & Evidence