Dimethylformamide → 9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3-carbaldehyde

HRID 1477332노트

반응식

HRID 1477332 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[Li]CCCC.CN([CH:30]=[O:31])C>C1COCC1>[CH3:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][N:6]1[C:5]2[CH:4]=[CH:3][C:2]([CH:30]=[O:31])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 708962893-bromo-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazoleHCID 178418339Butyllithium

생성물 1

HCID 866726799-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3-carbaldehyde수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 2a (1.5 g, 4.3 mmol) in dried THF (45 mL) was added n-BuLi (3.5 mL 5.2 mmol) at −78° C. The resulting mixture was stirred at −78° C. for 1 h and then added with dried DMF (3 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight before quenched with aqueous ammonia chloride solution. Water was added and extracted with ethyl acetate three times. The combined organic phase was washed with brine and dried over anhydrous sodium sulfate. After removing the solvent, the residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1:2) as eluent to afford 3a (0.76 g) as yellow solid in 60% yield. 1H NMR (400 MHz, CDCl3) δ 10.07 (s, 1H), 8.58 (d, J=0.8 Hz, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.98 (dd, J=8.8 Hz, 0.8 Hz, 1H), 7.51 (m, 3H), 7.30 (m, 1H), 4.53 (t, J=6.0 Hz, 2H), 3.87 (t, J=6.0 Hz, 2H), 3.49 (m, 2H), 3.38 (m, 2H), 3.26 (s, 3H). 13C NMR (400 MHz, CDCl3) δ 191.8, 144.3, 141.1, 128.5, 127.1, 126.6, 123.7, 123.0, 122.9, 120.6, 120.4, 109.4, 109.3, 71.8, 70.8, 69.1, 59.0, 43.4. MS (FAB) m/z Calcd for C18H19NO3 297.1. Found 297.3 [M]+.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. custombefore quenched with aqueous ammonia chloride solution
  4. additionWater was added
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic phase was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter removing the solvent
  9. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-f91d5eb015a14e569f0c1d250624fda2
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403794B2

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