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Dimethylformamide → Methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate

HRID 2221527
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HRID 2221527 반응식
[C:1]([C:9]1[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:11][C:10]=1[OH:29])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][C:15]=1[CH2:14][O:13][C:12]1[CH:27]=[CH:28][C:9]2[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:31]([C:32]([O:34][CH3:35])=[O:33])[O:29][C:10]=2[CH:11]=1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 230766154-(4-Benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole

생성물 1

HCID 69216315Methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate수율 55%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
90 °C

실험 절차

A mixture of 4-(4-benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole (54.93 g), methyl bromoacetate (32.88 g), potassium carbonate (19.76 g) and N,N-dimethylformamide (200 mL) was stirred at 90° 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. A mixture of the obtained residue, 1,8-diazabicyclo[5.4.0]-7-undecene (21.77 g), and toluene (750 mL) was heated under reflux for 20 hrs with azeotropic removal of water. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:8, v/v) to give methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate as colorless crystals (34.36 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 139-140° 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. additionA mixture of the obtained residue, 1,8-diazabicyclo[5.4.0]-7-undecene (21.77 g), and toluene (750 mL)
  6. temperaturewas heated
  7. temperatureunder reflux for 20 hrs with azeotropic removal of water
  8. concentrationThe reaction mixture was concentrated
  9. washeluted with ethyl acetate-hexane (1:8, v/v)

출처 및 근거

ORD 기록
ord-88ff7dfa634f426da606a03509aa1611
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07368578B2

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