Hydrochloric Acid → HCID 58026144, compound

Participants

Reaction Steps

To 19.1 g (0.057 mol) of acetic acid 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]-5-fluorobenzyl ester in 450 mL of DMSO at 15° C. was added 481 mL (0.240 mol) lithium trimethylsilylacetylide (0.5 M in THF). The mixture was warmed to room temperature and stirred for 3 hours. The mixture was then cooled to 0° C. and 300 mL of 3N NaOH was added and the mixture was stirred for 1 hour. The mixture was neutralized by the addition of 400 mL of 3N HCl. The organic phase was removed and the aqueous layers were extracted four times with diethyl ether. The organic phases were washed with 300 mL of water and 300 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 10-12% ethyl acetate/hexanes to afford 15 g (83%) of (S)-6-(4-fluoro-2-hydroxymethylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol.

Provenance & Evidence