Ethanol → Ethyl 1-ethyl-5-benzoyloxindole-3-carboxylate

HRID 236365

反応式

HRID 236365 の反応式
[Na].C(O)C.[C:5](=[O:12])([O:9][CH2:10][CH3:11])OCC.[CH2:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:22]=2)[CH2:17][C:16]1=[O:32])[CH3:14]>[Cl-].[Na+].O.C(Cl)Cl>[CH2:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:22]=2)[CH:17]([C:5]([O:9][CH2:10][CH3:11])=[O:12])[C:16]1=[O:32])[CH3:14]

参加物

7

反応物 4

HCID 702EthanolHCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 137705251-Ethyl-5-benzoyloxindole

生成物 1

HCID 20189466Ethyl 1-ethyl-5-benzoyloxindole-3-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
65 °C

実験手順

To a solution of 1.89 g. of sodium metal in 55 ml. of ethanol cooled to 0° C. was added 9.96 ml. of diethyl carbonate followed by 6.5 g. (27.43 mmoles) of 1-ethyl-5-benzoyloxindole. After heating for 2 hours at 65° C. on an oil bath, the reaction mixture was poured into a cold mixture of 250 ml. 1N hydrochloric, 250 ml. of a saturated brine solution and 200 ml. of methylene chloride. The organic phase was separated, dried and concentrated in vacuo. The excess diethylcarbonate was removed under high vacuum and the residue recrystallized from methylene chloride and cyclohexane, 2.1 g. 1st crop and 3.78 g. 2nd crop.

後処理

  1. additionwas added 9.96 ml
  2. additionthe reaction mixture was poured into a cold mixture of 250 ml
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe excess diethylcarbonate was removed under high vacuum
  7. customthe residue recrystallized from methylene chloride and cyclohexane, 2.1 g

出典と根拠

ORDレコード
ord-9a5217c5cdf744c18baacb6833f72fe2
出典データセット
uspto-grants-1987_02
特許番号
US04644005

関連ノート

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