反应详情

Butyl sulfide was generated by placing NaH (2.57 g, 0.11 mol) in a 500 ml round bottom flask, adding butanethiol (5.14 ml, 0.48 mol) and stirring for 5 minutes. DMF (200 mls) was added and the reaction heated at reflux. Slowly, 6-(6-methoxy-2-naphthyl)-6-oxo-hexanoic acid (Example 5) (7.2 g, 0.25 mol) in DMF (100 ml) was added to the reaction and heated at reflux for 1 hour. The methyl butyl sulfide and DMF were vacuum distilled (7 torr, 28° C.) to leave a bright yellow powder that was dissolved in water and precipitated with 5% HCl. The precipitate was filtered, dissolved in ethyl acetate (1800 ml), dried (Na2SO4), filtered and evaporated to give a yellow solid that was recrystallized (ethyl acetate) to give the title compound (5.38 grams, 79% yield), mp 191-193° C.; MS, m/e 272 (M+).

1. temperaturethe reaction heated
2. temperatureat reflux
3. temperatureheated
4. temperatureat reflux for 1 hour
5. distillationdistilled (7 torr, 28° C.)
6. customto leave a bright yellow powder that
7. customprecipitated with 5% HCl
8. filtrationThe precipitate was filtered
9. dissolutiondissolved in ethyl acetate (1800 ml)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. customevaporated
13. customto give a yellow solid
14. customthat was recrystallized (ethyl acetate)