反应详情

温度

110 °C

A RB flask fitted with reflux condenser containing tetrahydrocarbazole (1.71 g, 10.0 mol) was dissolved in DMSO (30 mL), treated with potassium tert-butoxide (1M solution in THF, 12 mL) and stirred at 110° C. for 20 min. Ethyl 6-bromohexanoate (1.67 mL, 10.0 mmol) was added and the mixture stirred at 110° C. for 60 min. The reaction was quenched with a 1:1 brine:water solution (120 mL) and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. Purification by column chromatography (25% ethyl acetate in hexane) afforded the title compound (1.01 g, 32%). 1H NMR (400 MHz, CDCl3): δ 7.52 (m, 1H), 7.27 (m, 1H), 7.19 (m, 1H), 7.12 (m, 1H), 4.18 (q, 2H, J=7.1 Hz), 4.04 (t, 2H, J=7.4 Hz), 2.78-2.73 (m, 4H), 2.33 (t, 2H, J=7.5 Hz), 2.00-1.92 (m, 4H), 1.80-1.75 (m, 2H), 1.72-1.66 (m, 2H), 1.42 (m, 2H), 1.30 (t, 3H, J=6.9 Hz). ESI-HRMS (m/z): [M+H]+ calcd. for C20H27NO2, 314.2115. found, 314.2103.

1. customA RB flask fitted
2. temperaturewith reflux condenser
3. stirringthe mixture stirred at 110° C. for 60 min
4. customThe reaction was quenched with a 1:1 brine
5. extractionwater solution (120 mL) and extracted with ethyl acetate
6. washThe combined organic extracts were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customPurification by column chromatography (25% ethyl acetate in hexane)