反应详情

温度

100 °C

A solution containing methyl 5-bromo4-oxo-4,5,6,7-tetrahydro-1-benzothiophene-5-carboxylate (Preparation 12, 1.18 g) and lithium carbonate (1.81 g) in anhydrous DMF (10 mL) is heated at 100° C. overnight. After cooling, the solids are removed by filtration and the filtrate is partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated to give a brown solid. This crude product is chromatographed on a Biotage column eluting with 0-20% ethyl acetate in heptane (250 mL each 10%) to give 270 mg (32%) of the title compound as a white solid. Physical characteristics: Mp 94-95° C.; MS (ESI−) m/z 207.0 (M−H)−. Anal. found: C, 57.26; H, 3.88; N, 0.17.

1. temperatureAfter cooling
2. customthe solids are removed by filtration
3. customthe filtrate is partitioned between ethyl acetate (50 mL) and water (50 mL)
4. washThe organic layer is washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a brown solid
9. customThis crude product is chromatographed on a Biotage column
10. washeluting with 0-20% ethyl acetate in heptane (250 mL each 10%)