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

HRID 236365

Reaction equation

HRID 236365 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9a5217c5cdf744c18baacb6833f72fe2
Source dataset
uspto-grants-1987_02
Patent number
US04644005

Linked notes

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