Potassium Hydroxide → HCID 15754179, compound

HRID 1084639Notes

Reaction equation

HRID 1084639 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([N:8]([CH2:18][CH2:19][C:20](=O)[CH3:21])[C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:7])[CH3:6].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([N:8]1[CH2:18][CH2:19][C:20]([CH3:21])=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]1=[O:17])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19978938HCID 19978938, compound

Product 1

HCID 15754179HCID 15754179, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.0 g (0.042 mol) of N-(3-chloro-α,α-dimethylbenzyl)-N-(3-oxobutyl)phenylacetamide prepared in accordance with the method of Reference Example 10, was dissolved in 100 ml of ethanol, and 1.3 g (0.02 mol) of potassium hydroxide powder was added thereto. The mixture was refluxed under heating for three hours. After completion of the reaction, ethanol as distilled off under reduced pressure, and then ice water was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then drived over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue thereby obtained was purified by chromatography by using a column packed with silica gel (n-hexane/ethyl acetate) to obtain 6.8 g (yield: 48.1%) of the desired compound.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for three hours
  3. distillationas distilled off under reduced pressure
  4. additionice water was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue thereby obtained
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-280e59e05893437287f03d28c888af6e
Source dataset
uspto-grants-1991_04
Patent number
US05006157

Reaction notes

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