Acetonitrile → 2-[3-(4'-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol

HRID 76885ノート

反応式

HRID 76885 の反応式
C([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C.Br[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1>C(Cl)Cl>[F:45][C:42]1[CH:43]=[CH:44][C:39]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][N:22]2[C:23]([CH2:25][CH2:26][OH:27])=[CH:24][N:20]=[CH:21]2)=[CH:40][CH:41]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanolHCID 114484672-Bromomethyl-4'-fluorobiphenyl

生成物 1

HCID 668864042-[3-(4'-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 2-(1-trityl-1H-imidazol-4-yl)ethanol (0.65 g, 1.80 mmol), acetonitrile (9 mL) and CH2Cl2 (12 mL) is added a solution of 2-bromomethyl-4′-fluorobiphenyl (0.478 g, 1.80 mmol) in CH2Cl2 (2 mL). The resulting mixture is stirred at room temperature overnight. The solution is concentrated and the residue is taken up in MeOH and heated to 75° C. for 3.5 h. The solution is then concentrated and the residue is partitioned between CH2Cl2 and aqueous 5% NaHCO3. The aqueous layer is then extracted with CH2Cl2 (3×). The combined organic layers are then washed with brine and dried over Na2SO4. The residue is then purified by flash chromatography (CH2Cl2/MeOH) give 2-[3-(4′-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol. MS (ESI) m/z 297.1 (M+H).

後処理

  1. concentrationThe solution is concentrated
  2. temperatureheated to 75° C. for 3.5 h
  3. concentrationThe solution is then concentrated
  4. customthe residue is partitioned between CH2Cl2 and aqueous 5% NaHCO3
  5. extractionThe aqueous layer is then extracted with CH2Cl2 (3×)
  6. washThe combined organic layers are then washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe residue is then purified by flash chromatography (CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-deba95d6e0b3463e83bf8667bbefda2a
出典データセット
uspto-grants-2014_09
特許番号
US08835646B2

反応ノート

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