Dimethylformamide → Methyl 5-(5-methyl-2-phenyl-4-oxazolyl)methoxy-3-pyridinecarboxylate

HRID 349950

反応式

HRID 349950 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1.Cl[CH2:13][C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][C:18]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:19][C:18]1[O:17][C:16]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:15][C:14]=1[CH2:13][O:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

生成物 1

HCID 17861341Methyl 5-(5-methyl-2-phenyl-4-oxazolyl)methoxy-3-pyridinecarboxylate収率 59.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 5-hydroxy-3-pyridinecarboxylate (9.84 g), 4-chloromethyl-5-methyl-2-phenyloxazole (13.40 g), potassium carbonate (8.90 g) and N,N-dimethylformamide (100 ml) was stirred at 80° C. overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain methyl 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridinecarboxylate (12.42 g, yield 59%) as pale yellow crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 119–120° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-4b6f402531fb40e68251360b27c030a2
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

関連ノート

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