Water → Trans-[4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman-3-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

2-[(4-Chloro-phenylsulfanyl)-(2,3,6-trifluoro-phenyl)-methyl]-propane-1,3-diol (6.2 g, 14.8 mmole) was dissolved in 150 mL THF and NaH (60% in oil, 2 g) was added. The reaction was stirred at 60° C. for four hours. 300 mL of water and 400 mL of EtOAc were added. The organic layer washed with brine (100 mL), dried over Na2SO4 and concentrated. The product was purified by column chromatography (EtOAc/hexane from 0/100 to 50/50 in 45 minutes). Yield: 5.0 g, 85%. 1H NMR (CDCl3 400 MHz) δ 7.45 (d, J=8.1 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H), 6.97 (m, 1H), 6.58 (m, 1H), 4.62 (dd, J=11.7 and 2.2 Hz, 1H), 4.50 (br, 1H), 4.43 (td, J=11.7 and 2.2 Hz, 1H), 3.67 (m, 1H), 3.48 (m, 1H), 2.25 (m, 1H), 1.50 (t, J=5.1 Hz, 1H).

Provenance & Evidence