Benzyl Bromide → Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate

HRID 2395070노트

반응식

HRID 2395070 반응식
[OH:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18973722Methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate

생성물 1

HCID 18973721Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate수율 62.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate (1.1 g, 4.3 mmol) in DMF (30 ml) was treated with benzyl bromide (0.89 g, 5.2 mmol) and potassium carbonate (0.72 g, 5.2 mmol). The reaction was stirred at ambient temperature overnight and then, partitioned between EtOAc/water. The organic phase was washed well with water, dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2) eluting with CH2Cl2 /EtOAc to give methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.94 g, 53%) as a low melting yellow solid.

후처리

  1. custompartitioned between EtOAc/water
  2. washThe organic phase was washed well with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2)
  6. washeluting with CH2Cl2 /EtOAc

출처 및 근거

ORD 기록
ord-4ad259ec389f4581ada1be4e095ffadb
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05811459

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