Water → 2-(1,1-Dimethyl-3-hydroxy-3-trifluoromethyl-5-hexynyl)-4-fluorotoluene

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Reaction Steps

Aluminum foil (324 mg, 12 mmol) and mercuric chloride (5.0 g, 0.02 mmol) were added to THF (6 mL) and vigorously stirred for 1 hour. Propargyl bromide (1.34 mL, 80% in toluene, 12 mmol) in 6 mL of THF was added slowly and the mixture heated up. After completion of the addition, the mixture was stirred for 2 hours at 40° C. and for 3 hours at room temperature. Half of the generated suspension was added via syringe to a solution of 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-one (500 mg, 1.91 mmol) in 20 mL of diethyl ether at −78° C. The reaction mixture was warmed up slowly to room temperature overnight. Water (20 mL) and ethyl acetate (20 mL) were added slowly. The organic phase was separated and the aqueous layer was extracted with two 10 mL portions of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed to give 6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (580 mg, 100%) as a colorless oil.

Provenance & Evidence