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

HRID 349950

반응식

HRID 349950 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b6f402531fb40e68251360b27c030a2
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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