反应详情

温度

130 °C

A mixture of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (18.8 g, 72.75 mmol), (3R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate (18.5 g, 76.4 mmol) and potassium carbonate (20.08 g, 145.5 mmol) in butyronitrile (250 mL) was heated to 130° C. for 3 hours. The solvent was removed in vacuo and ethyl acetate added. The organics were washed with water (40 mL), 0.5M sodium hydroxide solution (40 mL), brine (40 mL), dried (MgSO4), filtered and the solvent removed in vacuo. The residue was chromatographed on silica, eluting with a gradient of 0-5% methanol in DCM, to give the desired compound as a colourless oil (20.1 g). 1H NMR δ (CDCl3): 2.08-2.26 (m, 2H), 3.78-4.01 (m, 4H), 3.90 (s, 3H), 4.92-4.96 (m, 1H), 5.08 (s, 2H), 6.69 (t, 1H), 7.15 (t, 1H), 7.29 (t, 1H), 7.34-7.44 (m, 5H); m/z 327 (M+H)+

1. customThe solvent was removed in vacuo and ethyl acetate
2. additionadded
3. washThe organics were washed with water (40 mL), 0.5M sodium hydroxide solution (40 mL), brine (40 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customthe solvent removed in vacuo
7. customThe residue was chromatographed on silica
8. washeluting with a gradient of 0-5% methanol in DCM