Water → HCID 23076449, 화합물

HRID 2221664노트

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HRID 2221664 반응식
[CH2:1]([C:3]1[S:4][CH:5]=[C:6]([CH2:8]P(=O)(OCC)OCC)[N:7]=1)[CH3:2].[H-].[Na+].[CH3:19][O:20][CH2:21][O:22][C:23]1[C:27]([CH:28]=O)=[CH:26][N:25]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1.O>O1CCCC1>[CH2:1]([C:3]1[S:4][CH:5]=[C:6](/[CH:8]=[CH:28]/[C:27]2[C:23]([O:22][CH2:21][O:20][CH3:19])=[N:24][N:25]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=2)[N:7]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 230765133-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 85954626Phosphonic acid, [(2-ethyl-4-thiazolyl)methyl]-, diethyl ester

생성물 1

HCID 23076449HCID 23076449, 화합물수율 74.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of diethyl [(2-ethyl-1,3-thiazol-4-yl)methyl]phosphonate (4.64 g) in tetrahydrofuran (75 mL) was added sodium hydride (60% in oil, 0.96 g) at room temperature, and the mixture was stirred for 30 min. 3-(Methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde (6.32 g) was added to the reaction mixture, and the mixture was heated under reflux 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 (1:9-1:1, v/v) to give 2-ethyl-4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole as a pale-yellow oil (4.49 g, yield 66%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. washeluted with ethyl acetate-hexane (1:9-1:1

출처 및 근거

ORD 기록
ord-245ffa23a67c49baa0cadc06efe7c81b
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368578B2

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