Sodium Hydroxide → (S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

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Reaction Steps

2,3-Epoxy-1,1,1-trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)butane (1.68 g) was dissolved in 250 mL ethanol and 150 mL 6N NaOH was added. The mixture was stirred for 2 hours, and 500 mL of saturated aqueous. NaHCO3 was added. The mixture was extracted with ether and the organic layers were combined, dried, and evaporated to yield the title compound as a white solid (1.2 g, 70%); [α]23 =-28.35 (c=1.05, MeOH); NMR (CDCl3): 7.93-7.85 (m,4, Ar), 7.58-7.45 (m,5, Ar), 6.90-6.84 (d,1, vinylic), 6.40-6.34 (d,1, vinylic), 2.75 (s,1, OH), 1.55 (s,3, CH3); MS: m/z=357(M+1).

Provenance & Evidence