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

HRID 1477328Notes

Reaction equation

HRID 1477328 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-94f7c416c7d54a1b935a474ccf409434
Source dataset
uspto-grants-2016_08
Patent number
US09403794B2

Reaction notes

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