反应详情

A mixture of 6.23 g (25 mmol) of 9c and 5.71 g (50 mmol) of potassium thiolacetate in 100 mL of acetone was heated at reflux for 30 minutes. After cooling to room temperature, the crude reaction mixture was filtered, and the filtrate was concentrated, in vacuo. The residue obtained was partitioned between ether and water (150 mL each). The layers were separated and the aqueous phase was extracted with 100 mL of ether and 100 mL of ethyl acetate. The combined organic extracts were dried over Na2SO4 and concentrated, in vacuo, yielding a red oil which was purified by flash chromatography. Elution with hexane/ethyl acetate (9:1) yielded the product as a yellow solid (5.61 g, 92% yield) mp 67°-68° C.

1. temperaturewas heated
2. temperatureat reflux for 30 minutes
3. customthe crude reaction mixture
4. filtrationwas filtered
5. concentrationthe filtrate was concentrated, in vacuo
6. customThe residue obtained
7. customwas partitioned between ether and water (150 mL each)
8. customThe layers were separated
9. extractionthe aqueous phase was extracted with 100 mL of ether and 100 mL of ethyl acetate
10. dry with materialThe combined organic extracts were dried over Na2SO4
11. concentrationconcentrated, in vacuo
12. customyielding a red oil which
13. customwas purified by flash chromatography
14. washElution with hexane/ethyl acetate (9:1)