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

HRID 1023879

反応式

HRID 1023879 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-18c8311c33fb4c8189ea729acebbafff
出典データセット
uspto-grants-2014_05
特許番号
US08722720B2

関連ノート

読み込み中…