Iodopentafluoroethane → HCID 23324899, compound

Participants

Reaction Steps

Gaseous pentafluoroethyl iodide (5 g., 0.02M) was passed into a flask containing dry ether (40 ml.) at -70° and fitted with a dry-ice condenser. A 3 molar solution of methylmagnesium bromide (5.8 ml., 0.017M) was then added over 5 minutes keeping the temperature between -70° and -65°. The mixture was then stirred at -70° for 1/2 hour. 1-Ethoxycarbonyl-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol (1.3 g., 0.0047M) in dry ether (10 ml.) was then added over 10 minutes keeping the temperature at -65° or below. The mixture was then stirred at -70° for 1 hour and was then allowed to warm to -25° over 11/2 hours. A solution of ammonium chloride (5 g.) in water (30 ml.) was then added. The ether layer was separated and the aqueous layer was extracted further with ether (2×40 ml.). The ether layers were combined, dried (MgSO4) and evaporated to give the crude title compound as an oil. The oil was purified by chromatography on silica (230-400 mesh) eluting with ethyl acetate:60°-80° petrol (4:1, by volume) to give the title compound, 1.2 g (55% yield). The compound was recrystallised from cyclohexane, m.p. (after said recrystallisation) 128°-132°.

Provenance & Evidence