반응 #498376

반응 방정식

methyl 5-bromo4-oxo-4,5,6,7-tetrahydro-1-benzothiophene-5-carboxylate

lithium carbonate

→

title compound

수율 32.0%

Methyl 4-hydroxy-1-benzothiophene-5-carboxylate

수율 32.0%

용매

DMF

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   기타the solids are removed by filtration
3. 3
   기타the filtrate is partitioned between ethyl acetate (50 mL) and water (50 mL)
4. 4
   세척The organic layer is washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to give a brown solid
9. 9
   기타This crude product is chromatographed on a Biotage column
10. 10
    세척eluting with 0-20% ethyl acetate in heptane (250 mL each 10%)

실험 절차

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.

출처