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

HRID 2395070ノート

反応式

HRID 2395070 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ad259ec389f4581ada1be4e095ffadb
出典データセット
uspto-grants-1998_09
特許番号
US05811459

反応ノート

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