Water → HCID 23076600、化合物

HRID 2221673ノート

反応式

HRID 2221673 の反応式
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9]P(=O)(OCC)OCC)[N:8]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:20][O:21][CH2:22][O:23][C:24]1[C:28]([CH:29]=O)=[CH:27][N:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:25]=1.O>O1CCCC1>[CH:1]([C:4]1[S:5][CH:6]=[C:7](/[CH:9]=[CH:29]/[C:28]2[C:24]([O:23][CH2:22][O:21][CH3:20])=[N:25][N:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:27]=2)[N:8]=1)([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2763198Diethyl 2-isopropylthiazole-4-methylphosphonateHCID 230765133-(methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 23076600HCID 23076600、化合物収率 60.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of diethyl [(2-isopropyl-1,3-thiazol-4-yl)methyl]phosphonate (2.47 g) in tetrahydrofuran (100 mL) was added sodium hydride (60% in oil, 0.36 g) at room temperature, and the mixture was stirred for 30 min. 3-(Methoxymethoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde (1.72 g) was added to the reaction mixture and the mixture was heated under reflux for 2 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 (1:3, v/v) to give 2-isopropyl-4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole as pale-yellow oil (1.59 g, yield 60%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 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 (1:3

出典と根拠

ORDレコード
ord-165a0e3d186642c58aba1cb66a37bca8
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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