Diethyl Ether → HCID 18957140, compound

Participants

Reaction Steps

To a stirred, room temperature suspension of pyridinium chlorochromate (0.720 g, 0.00334 mol) and anhydrous sodium acetate (0.0546 g, 0.000666 mol) in dichloromethane (6 mL) was added dropwise over 20 minutes a solution of N'-[2,6-bis(1-methylethyl)-phenyl]-N-[2-(8-hydroxyoctyl)-2H-tetrazol-5-yl]-N-phenyl-urea (1.09 g, 0.00221 mol) in dichloromethane (6 mL), and the mixture was stirred. After 2 hours, diethyl ether (4 mL) was added and the mixture was filtered through celite. The filtercake was washed with dichloromethane. The filtrate and washings were rotoevaporated, and the residue was chromatographed on silica gel (135 g, 230-400 mesh) using PET etherdiethyl ether (1:2, 15-125 mL) as eluent. Fractions containing product were rotoevaporated from dichloromethane to an oil. The oil was dried in vacuo wherein it solidified, yield 0.7108 g (65%) of the title compound, mp=104°-106° C.

Provenance & Evidence