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

HRID 333769노트

반응식

HRID 333769 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 241Benzene용매

반응 조건

온도
50 °C

실험 절차

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+].

후처리

  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%))

출처 및 근거

ORD 기록
ord-65fa3181611f414e8c47023216c95f6a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883786B2

반응 노트

불러오는 중…