Hydrochloric Acid → 2-Methyl-1-phenoxybut-3-yn-2-ol

Participants

Reaction Steps

To 3.1 parts of triethylsilylacetylene in 15 parts by volume of ether at -30° C. is added 8 parts by volume of 2.5 molar n-butyl lithium. The reaction mixture is allowed to come to room temperature and 3 parts of phenoxyacetone in 5 parts by volume of ether is added. The reaction mixture is stirred at room temperature for one hour and then poured into ether and dilute (1 N) hydrochloric acid solution. The ether layer is washed with water and dried over anhydrous sodium sulfate. The solvents are removed at reduced pressure and the residual oil is dissolved in 15 parts by volume of dimethylformamide containing about 5 parts of powdered potassium fluoride. The reaction mixture is stirred at 70°-80° C. for about 1 hour. The reaction mixture is worked up by diluting with ether and washing several times with water. The ether layer is dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure. The residual oil is isolated by low pressure liquid chromatography on silica gel using 30% ethyl acetate/hexane as eluent to provide 3-hydroxy-3-methyl-4-phenoxy-1-butyne.

Provenance & Evidence