反应详情

A solution of 6,7-dihydro-4(5H)-benzofuranone (0.10 g, 0.73 mmol), carbon disulfide (0.048 mL, 0.80 mmol), and iodomethane (0.10 mL, 1.6 mmol) in tetrahydrofuran (1.8 mL) was treated with a 60% dispersion of sodium hydride in mineral oil (0.070 g, 1.8 mmol), stirred over night at ambient temperature and partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), filtered and concentrated. The residue was treated with guanidine nitrate (0.36 g, 2.9 mmol), treated with 1.46 mL (2.2 mol) of 1.5 M sodium ethoxide in ethanol, heated to 80° C. overnight, cooled, diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layers were dried (magnesium sulfate), filtered, concentrated and chromatographed using ethyl acetate in dichloromethane to provide the title compound: 1H NMR (300 MHz, CDCl3) δ 2.52 (s, 3H), 2.88-3.02 (m, 4H), 5.07 (br s, 2H), 6.87 (d, J=1.7 Hz, 1H), 7.37 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 234 (M+H)+.

1. custompartitioned between saturated ammonium chloride and ethyl acetate
2. washThe organic layer was washed with brine
3. dry with materialdried (magnesium sulfate)
4. filtrationfiltered
5. concentrationconcentrated
6. temperatureheated to 80° C. overnight
7. temperaturecooled
8. extractionextracted with dichloromethane (3×)
9. dry with materialThe combined dichloromethane layers were dried (magnesium sulfate)
10. filtrationfiltered
11. concentrationconcentrated
12. customchromatographed