Tetrahydrofuran → HCID 23324898, compound

Participants

Reaction Steps

2-(2,4-Difluorophenyl)-2-hydroxy-4,4,5,5,5-pentafluoro-1-(1H-1,2,4-triazol-1-yl)pentan-3-one (0.5 g; 0.00135 moles) was dissolved in sodium-dried diethyl ether (50 cm3) and methylmagnesium bromide (1.35 cm3 of a 3M solution in ether; 0.00405 moles) was added. Dry tetrahydrofuran (15 cm3) was then added. The mixture was heated at reflux for 2 hours, cooled and 5% aqueous ammonium chloride (50 cm3) was added, followed by ethyl acetate (100 cm3). The phases were separated and the organic phase was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on 230-400 mesh silica, eluting with ethyl acetate:diethylamine (95:5, 500 cm3). Two diastereomers were recovered by collection and evaporation of appropriate fractions. The first diastereomer to be eluted was called diastereomer I.

Provenance & Evidence