Acetylene → HCID 13116850, compound

Participants

Reaction Steps

Acetylene was passed into a suspension of 31.4 g (0.28 mol) of potassium tert-butylate in 300 ml of tetrahydrofuran for 30 minutes at 15° C., while stirring. A solution of 55.5 g (0.2 mol) of 1-(4-fluorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one in 150 ml of tetrahydrofuran was then added dropwise in the course of one hour, while acetylene was further passed through the mixture. After a further two hours, the solution was adjusted to a pH value of 8 by the addition of 175 ml of a 23% strength aqueous ammonium chloride solution. The mixture was extracted with twice 200 ml of ethyl acetate, the extracts were washed with water, and the solution was concentrated under reduced pressure. The remaining solid residue was triturated with petroleum ether. 27.2 g (44.8% of theory) of 3-((4-fluorophenoxy)-(1H-1,2,4-triazol-1-yl)-methyl)-4,4-dimethyl-pent-1-yn-3-ol of melting point 155° to 161° C. were thus obtained. By cooling and triturating, a further 3.2 g (5.3% of theory) of a pure diastereomeric form A of melting point 134° to 135° C. were obtained from the petroleum ether phase.

Provenance & Evidence