Sodium hydride → 1-(benzofuran-3-yl)-2-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)ethanone

HRID 1023879

반응식

HRID 1023879 반응식
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[C:36]([C:43](=[O:46])[CH2:44]Br)=[CH:35]1>CN(C=O)C.O>[O:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[C:36]([C:43](=[O:46])[CH2:44][O:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:23]2[N:22]=[CH:21][N:20]([C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:24]=2)=[CH:35]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 27765801-(Benzofuran-3-yl)-2-bromoethanoneHCID 582940602-(1-trityl-1H-imidazol-4-yl)phenol

생성물 1

HCID 672075921-(benzofuran-3-yl)-2-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)ethanone수율 60%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-(1-trityl-1H-imidazol-4-yl)phenol (0.5 mmol) in anhydrous DMF (3 mL) at 0° C. was added NaH (36.0 mg, 0.75 mmol). The resulting suspension was allowed to stir for 10 min. To the resulting solution was added 1-(benzofuran-3-yl)-2-bromoethanone (0.50 mmol). After stirring overnight, the reaction mixture was carefully diluted, with water and extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water, brine and dried (Na2SO4). The solvent was removed under reduced pressure and the crude product was purified by column chromatography. Yield 60%. 1H NMR: 5.16 (s, 2H), 6.88 (d, 1H, J=8.10 Hz), 7.06-7.47 (m, 20H), 7.54 (d, 2H, J=7.92 Hz), 8.22 (dd, 2H, J=7.60 Hz, 1.35 Hz), 8.33 (s, 1H).

후처리

  1. stirringAfter stirring overnight
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-18c8311c33fb4c8189ea729acebbafff
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722720B2

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