反应详情

温度

80 °C

A mixture of 6-bromo-2-naphthyl hydrosulfide (Example 5 Step 2, 1.80 g, 7.53 mmol), (1S)-1-(2-iodophenyl)ethanol (1.82 g, 7.34 mmol), copper(I) iodide (70 mg, 0.37 mmol) and potassium carbonate (2.02 g, 14.6 mmol) was degassed then isopropyl alcohol (10 mL) and ethylene glycol (0.82 mL, 14.7 mmol) added. The reaction was heated to 80° C. overnight. The cooled reaction mixture was diluted with ethyl acetate (40 mL), filtered and concentrated in vacuo. The residue was purified by flash column chromatography, eluting with a 10-20% ethyl acetate/isohexane gradient to give solid (1S)-1-{2-[(6-bromo-2-naphthyl)thio]phenyl}ethanol (2.30 g, 85%). 1H NMR (400 MHz, CDCl3) δ 7.94 (1H, s), 7.68 (1H, dd, J 1.4, 7.8), 7.64 (1H, d, J 8.7 Hz), 7.58-7.50 (3H, m), 7.43-7.39 (1H, m), 7.36 (1H, dd, J 1.4, 7.8 Hz), 7.30 (1H, dd, J 1.8, 8.6 Hz), 7.27-7.23 (1H, m), 5.44 (1H, q, J 6.3 Hz), 1.46 (3H, d, J 6.4 Hz); m/z (ES+) 341, 343 [(M-OH)+].

1. customwas degassed
2. customThe cooled reaction mixture
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was purified by flash column chromatography
6. washeluting with a 10-20% ethyl acetate/isohexane gradient