反应详情

温度

40 °C

A solution of the compound of formula 5, 1-ethyl 1,2,3,4-tetrahydrocarbazole-1-acetic acid (2.0 g, 7.4 mmole), described in Example 56, in dry tetrahydrofuran (THF, 50 ml) is added dropwise under nitrogen to a stirred suspension of sodium hydride (1 g, 50% dispersion, 0.02 mole) in dry-THF (25 ml). The reaction mixture is stirred for 15 minutes after the end of the addition. The lower alkyl halide, methyliodide (1.5 ml), is added dropwise. The reaction mixture is heated initially to 40° C. then stirred for one hour at room temperature. A small amount of water is added cautiously to destroy excess sodium hydride followed by the addition of more water (50 ml). The mixture is washed with ether then rendered acidic and extracted with ether. The ether extract is dried (MgSO4), treated with charcoal and filtered through diatomaceous earth. Evaporation of the ether gives an oil which on recrystallization from benzene affords the title compound, mp 140°-143° C., nmr (CDCl3) δ 0.72 (t, J = 7, 3H), 1.9 (m, 6H), 2.75 (m, 4H), 3.76 (s, 3H), 7.2 (m, 4H).

1. dry with materialin dry-THF (25 ml)
2. additionafter the end of the addition
3. additionThe lower alkyl halide, methyliodide (1.5 ml), is added dropwise
4. stirringthen stirred for one hour at room temperature
5. additionA small amount of water is added cautiously
6. customto destroy excess sodium hydride
7. additionfollowed by the addition of more water (50 ml)
8. washThe mixture is washed with ether
9. extractionextracted with ether
10. extractionThe ether extract
11. dry with materialis dried (MgSO4)
12. additiontreated with charcoal
13. filtrationfiltered through diatomaceous earth
14. customEvaporation of the ether
15. customgives an oil which
16. customon recrystallization from benzene