Dimethylformamide → ethyl 1-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxylate

HRID 2221740노트

반응식

HRID 2221740 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[O:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[O:11][C:12]=1[CH3:13].[CH2:22]([N:29]1[CH:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:31]([OH:39])=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:22]([N:29]1[CH:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:31]([O:39][CH2:2][C:3]2[CH:21]=[CH:20][CH:19]=[C:5]([O:6][CH2:7][C:8]3[N:9]=[C:10]([C:14]4[O:15][CH:16]=[CH:17][CH:18]=4)[O:11][C:12]=3[CH3:13])[CH:4]=2)=[N:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076545HCID 23076545, 화합물HCID 178469738HCID 178469738, 화합물

생성물 1

HCID 69217587ethyl 1-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxylate수율 79%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-(3-chloromethylphenoxy)methyl-2-(2-furyl)-5-methyl-1,3-oxazole (2.04 g), ethyl 1-benzyl-3-hydroxy-1H-pyrazole-4-carboxylate (1.50 g), potassium carbonate (0.84 g) and N,N-dimethylformamide (50 mL) was stirred at 80° C. for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2, v/v) to give ethyl 1-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzyl)oxy]-1H-pyrazole-4-carboxylate as colorless crystals (2.46 g, yield 79%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 92-93° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:2

출처 및 근거

ORD 기록
ord-c2664293d1584a3284662cd485b5133d
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368578B2

반응 노트

불러오는 중…