反应详情

To an ice cold solution of Example 236B (4.2 g, 17 mmol) in anhydrous tetrahydrofuran (42 mL) under nitrogen atmosphere was added methyl thioglycolate (1.83 mL, 20.4 mmol) followed by powdered cesium carbonate (6.65 g, 20.4 mmol). Then the reaction mixture was allowed to warm to room temperature with stirring under nitrogen. After 30 minutes the reaction was refluxed for 15 minutes and cooled to room temperature. The reaction mixture was quenched with ice (50 mL) and partitioned with ethyl acetate (250 mL). The organic layer separated was washed with an ice cold solution of saturated NaCl (3×60 mL), dried (Na2SO4), and concentrated under reduced pressure to obtain the crude product which was recrystallized from methanol. The mother liquor was purified by flash chromatography on silica gel eluting with 7% acetone-hexane. The combined fractions gave the title compound in 55% yield (3.07 g). MS (APCI) m/e: 300 (M+H)+; 1H NMR (300 MHz, DMSO-d6) d: 3.92 (s, 3H), 5.42 (s, 2H), 7.35-7.47 (m, 3H), 7.52-7.57 (m, 2H, Ar—CH), 8.12 (s, 1H,), 8.36 (s, 1H), 8.98 (s, 1H).

1. temperatureAfter 30 minutes the reaction was refluxed for 15 minutes
2. temperaturecooled to room temperature
3. customThe reaction mixture was quenched with ice (50 mL)
4. custompartitioned with ethyl acetate (250 mL)
5. customThe organic layer separated
6. washwas washed with an ice cold solution of saturated NaCl (3×60 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customto obtain the crude product which
10. customwas recrystallized from methanol
11. customThe mother liquor was purified by flash chromatography on silica gel eluting with 7% acetone-hexane