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

HRID 1749238ノート

反応式

HRID 1749238 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23]>CN(C=O)C>[CH3:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

参加物

5

反応物 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 94934Ethane, 1-(2-chloroethoxy)-2-methoxy-

生成物 1

HCID 588035919-(2-(2-methoxyethoxy)ethyl)-9H-carbazole収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  1. temperatureAfter cooling down to 0° C.
  2. customthe reaction mixture was carefully quenched with water
  3. extractionextracted with ethyl acetate three times
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialThen the organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-a5b4dc821e4744eda9f7a272e8e675b5
出典データセット
uspto-grants-2015_10
特許番号
US09156814B2

反応ノート

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