Potassium Carbonate → HCID 70353795, compound

HRID 2309391Notes

Reaction equation

HRID 2309391 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:26])=[C:9]([CH2:12][CH2:13][CH2:14]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)[CH2:5][C:4]1=[O:27])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]3[O:26][CH2:14][CH:13]=[CH:12][C:9]=3[CH:10]=2)[CH2:5][C:4]1=[O:27])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20185114HCID 20185114, compound

Product 1

HCID 70353795HCID 70353795, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.65 g. (4.41 mmoles) of 1-ethyl-5-hydroxy-6-(3-tosyloxypropyl)oxindole and 610 mg. (4.41 mmoles) of potassium carbonate in 90 ml. of acetone was heated at reflux for 2.5 hours. The reaction was cooled, filtered and the filtrate evaporated. The crude residue was purified by chromatographing on 100 g. of silica gel, using 66% diethyl ether-hexane as the eluent, to give 571 mg. (60% yield) of the desired intermediate.

Workup

  1. additionA mixture of 1.65 g
  2. temperatureat reflux for 2.5 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe crude residue was purified by chromatographing on 100 g
  7. customto give 571 mg

Sources & evidence

ORD record
ord-ddd2db1f5bb24722a2cbff509446ce72
Source dataset
uspto-grants-1987_09
Patent number
US04695571

Reaction notes

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