1-Pentyne → 2,2-Dimethyl-1-fluoro-3-hydroxy-3-(pent-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)butane

Participants

Reaction Steps

To a stirred solution of pent-1-yne (1.5 g, 22 mmol) in dry tetrahydrofuran (40 ml) was added n-butyl lithium (9 ml of 2.6M, 23 mmol) at -78° C. under a nitrogen atmosphere followed by chlorotitanium tri-isopropoxide (22 ml of 1M, 20 mmol). After 15 minutes, a solution of 3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)butan-2-one (prepared as in DE 2,820,361) (4.0 g, 22 mmol) in dry tetrahydrofuran (20 ml) was added dropwise. Upon complete addition the mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was then poured onto ice and extracted with ether (2×250 ml). The ethereal solution was washed with saturated brine solution then dried over anhydrous magnesium sulphate and the solvent removed. The resulting yellow oil was chromatographed (silica gel, petrol/diethyl ether elution) to give a yellow gum (2.8 g).

Provenance & Evidence