Tetrabutylammonium Fluoride → HCID 67571000, compound

Participants

Reaction Steps

A stirred solution of E-1-bromo-3(1-trityl-1,2,4-triazol-3-yl)prop-2-ene) (34.47 g, prepared as described in Example 12) in dry dichloromethane (150 ml) was treated, under nitrogen, with tetrabutylammonium fluoride (160 ml, 1M in tetrahydrofuran). The mixture was heated under reflux for thirty minutes, cooled, washed with water (3×100 ml), dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ether (25:2) as eluant, to give E-1-fluoro-3(1-trityl-1,2,4-triazol-3-yl)prop-2-ene (19.37 g, m.p. 149° C). NMR (CDCl3): δ 4.95, 5.15(2H,dd), 6.7-6.9(2H,m), 7.1-7.3(15H,m), 7.9(1H,s). JCH=CH 16.1 Hz, JHF 46.8 Hz. 19F NMR (CDCl3): -216.4 ppm vs. CFCl3.

Provenance & Evidence