반응 #1836420

반응 방정식

1-chloro-2-(2-methoxyethoxy)ethane

carbazole

NaH

→

alkylated carbazole

수율 83.0%

9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

수율 83.0%

용매

DMF

반응 조건

후처리

1. 1
   온도After cooling down to 0° C.
2. 2
   기타the reaction mixture was carefully quenched with water
3. 3
   추출extracted with ethyl acetate three times
4. 4
   세척The combined organic phase was washed with water and brine
5. 5
   건조Then the organic layer was dried over anhydrous sodium sulfate
6. 6
   기타the solvent was removed
7. 7
   기타The residue was purified by silica gel chromatography

실험 절차

To a solution of carbazole (3.34 g, 20 mmol) in DMF (80 mL) at 0° C. was added NaH (0.72 g, 30 mmol). After heating to 80° C. for 1.5 h, 1-chloro-2-(2-methoxyethoxy)ethane (3.31 g, 24 mmol) was added dropwise. The resulting mixture was kept at 80° C. overnight. After cooling down to 0° C., the reaction mixture was carefully quenched with water and extracted with ethyl acetate three times. The combined organic phase was washed with water and brine. Then the organic layer was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using petroleum ether and ethyl acetate as eluent (EA:PE=1:3) to afford alkylated carbazole 1a (4.46 g) as brown oil in 83% yield. 1H NMR (400 MHz, CDCl3) δ 8.09 (d, J=7.6 Hz, 2H), 7.46 (m, 4H), 7.23 (m, 2H), 4.51 (t, J=6.4 Hz, 2H), 3.86 (t, J=6.4 Hz, 2H), 3.52 (m, 2H), 3.42 (m, 2H), 3.31 (s, 3H). 13C NMR (400 MHz, CDCl3) δ 140.5, 125.6, 122.8, 120.2, 118.9, 108.7, 71.8, 70.7, 69.1, 59.0, 43.0. MS (FAB) m/z Calcd for C17H19NO2 269.1. Found 269.2 [M]+.

출처