Imidazole → 2-(4-Hydroxy-phenyl)-7-imidazol-1-ylmethyl-benzofuran-5-ol

HRID 1835979ノート

反応式

HRID 1835979 の反応式
Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[C:5]([OH:19])[CH:4]=1.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.O>CN(C=O)C>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[O:10][C:11]3[C:3]([CH2:2][N:20]4[CH:24]=[CH:23][N:22]=[CH:21]4)=[CH:4][C:5]([OH:19])=[CH:6][C:7]=3[CH:8]=2)=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 962WaterHCID 10171939HCID 10171939、化合物

生成物 1

HCID 101496022-(4-Hydroxy-phenyl)-7-imidazol-1-ylmethyl-benzofuran-5-ol収率 89.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of benzyl bromide 4 (0.070 g, 0.215 mmole) in 10 mL DMF was added imidazole (0.030 g, 0.437 mmole). After stirring at 60° C. for 3 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 9:1) to afford 0.059 g (88%) of imidazole 16 as a light tan solid: Mp=269-271° C.; 1H NMR (DMSO-d6) δ 9.88 (s, 1 H), 9.24 (s, 1 H), 7.88 (s, 1 H), 7.72 (d, 2 H, J=8.6 Hz), 7.26 (s, 1 H), 7.04 (s, 1 H), 6.93 (s, 1 H), 6.88 (d, 2 H, J=8.7 Hz), 6.83 (d, 1 H, J=2.3 Hz), 6.50 (d, 1 H, J=2.3 Hz), 5.46 (s, 2 H); MS 305 (M−H)−

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe organic phases were concentrated
  5. customchromatographed with silica gel (hexanes:ethyl acetate, 9:1)

出典と根拠

ORDレコード
ord-9507071d6c1c433d8ccba93cf65b43d5
出典データセット
uspto-grants-2004_08
特許番号
US06774248B2

反応ノート

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