1-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne → 4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

Beteiligte Stoffe

Reaktionsschritte

To a solution of sodium bis(2-methoxyethoxy)aluminum hydride (1.5 mL, 3.4M in toluene) in freshly distilled diethyl ether (6 mL) was added a solution of 1-(4-phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne in diethyl ether (6 mL) dropwise. The rate of addition was controlled so that the reaction temperature did not exceed 8° C. The mixture was stirred for 15 minutes and was quenched at 0° C. with 3N sulfuric acid (15 mL). Water (10 mL) was added and the product was extracted into diethyl ether. The combined organic extracts were washed (brine) and dried. The solvent was evaporated and the material was purified by chromatography, with chloroform:diethyl ether (25:1) as the eluent, to give the title compound (848 mg, 79%).

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