Benzyl Bromide → 1-(2-Benzyloxy-pyridin-4-yl)-2-(2,4-dichloro-phenyl)-propan-1-one

HRID 333769ノート

反応式

HRID 333769 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:19])[C:10]([C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[CH:13]=1)=[O:11].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:20]([O:18][C:14]1[CH:13]=[C:12]([C:10](=[O:11])[CH:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH3:19])[CH:17]=[CH:16][N:15]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 2

HCID 7498Benzyl BromideHCID 574213374-[2-(2,4-Dichloro-phenyl)-propionyl]-1H-pyridin-2-one

生成物 1

HCID 668132461-(2-Benzyloxy-pyridin-4-yl)-2-(2,4-dichloro-phenyl)-propan-1-one収率 59.8%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 241Benzene溶媒

反応条件

温度
50 °C

実験手順

This material was re-benzylated as follows: 4-[2-(2,4-Dichloro-phenyl)-propionyl]-1H-pyridin-2-one (100 mg) was dissolved in absolute benzene (6 mL) and silver carbonate (65 mg) and benzyl bromide (70 mg, 0.05 mL) were added. The mixture was stirred at 50° C. over night and was then poured into ice water. The aqueous phase was extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (20 g silica gel, gradient of ethyl aceate in heptane (0 to 20%)) to give 1-(2-benzyloxy-pyridin-4-yl)-2-(2,4-dichloro-phenyl)-propan-1-one (78 mg) as a colorless oil. MS (m/e)=386.0 [MH+].

後処理

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography (20 g silica gel, gradient of ethyl aceate in heptane (0 to 20%))

出典と根拠

ORDレコード
ord-65fa3181611f414e8c47023216c95f6a
出典データセット
uspto-grants-2014_11
特許番号
US08883786B2

反応ノート

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