Sulfuric Acid → Diethyl 1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate

HRID 373990ノート

反応式

HRID 373990 の反応式
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3]1.S(=O)(=O)(O)O.[C:23]1([NH:29]N)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.C(O)C>[CH2:6]1[C:7]2[NH:29][C:23]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:2]=2[CH2:3][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 516892Sodium BicarbonateHCID 14062941Diethyl 4-oxocyclohexane-1,2-dicarboxylate

生成物 1

HCID 19808697Diethyl 1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate収率 59.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 20 ml of ethanol were added 2.66 g of diethyl 4-oxocyclohexane-1,2-dicarboxylate, 2.45 g of concentrated sulfuric acid and 1.08 g of phenylhydrazine. The mixture was refluxed for 2 hours and then cooled to room temperature. Thereto were added 50 ml of ethyl acetate and 50 ml of water. The mixture was adjusted to pH 7.5 with an aqueous saturated sodium hydrogencarbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethanol to obtain 1.87 g (yield: 59%) of diethyl 1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate as colorless needles.

後処理

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe organic layer was separated
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-754ae980b0c441478053da60818f18c9
出典データセット
uspto-grants-1992_11
特許番号
US05166204

反応ノート

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