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

HRID 236365

반응식

HRID 236365 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a5217c5cdf744c18baacb6833f72fe2
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644005

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