Dimethylformamide → Ethyl 2-[[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenoxy]methyl]nicotinate

HRID 1294211ノート

反応式

HRID 1294211 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.Cl[CH2:23][C:24]1[N:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].CN(C)C=O.[H-].[Na+]>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:23][C:24]2[N:34]=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 13170694Ethyl 2-(chloromethyl)pyridine-3-carboxylateHCID 68884209HCID 68884209、化合物

生成物 1

HCID 68887469Ethyl 2-[[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenoxy]methyl]nicotinate収率 63.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenol (2.70 g), ethyl 2-chloromethylnicotinate (1.74 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 0.42 g) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give ethyl 2-[[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenoxy]methyl]nicotinate as a colorless oil (2.45 g, 63%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

後処理

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb338c8d565b4ac78301e129436b8e8e
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

反応ノート

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