Hydrochloric Acid → Ethyl alpha-(3-cyclopentyloxy-4-methoxybenzyl)-alpha-(4-methoxyphenacyl)acetate

HRID 1415824Notes

Reaction equation

HRID 1415824 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH2:10][C:11]([CH2:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:24])(C(OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1OCCOCCOCCOCCOCCOC1.[OH-].[K+].Cl>C1C=CC=CC=1.C(O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:33]=[CH:34][C:35]=2[O:36][CH3:37])[CH2:10][CH:11]([CH2:22][C:23]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[O:24])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 21862807HCID 21862807, compound

Product 1

HCID 21862879Ethyl alpha-(3-cyclopentyloxy-4-methoxybenzyl)-alpha-(4-methoxyphenacyl)acetateYield 81.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

2.43 g (4.7 mmol) of diethyl α-(3-cyclopentyloxy-4-methoxybenzyl)-α-(4-methoxyphenacyl)malonate [prepared as described in step (ii) above] and 1.26 g (4.7 mmol) of 18-crown-6 were dissolved in 50 ml of benzene, and 4.70 ml (4.7 mmol) of a 1.1M solution of potassium hydroxide in ethanol were added to the resulting solution. The mixture was then stirred for 30 minutes, after which the ethanol in the reaction mixture was removed by distillation under reduced pressure. The remaining reaction solution was heated under reflux for 14 hours and then the reaction mixture was cooled to room temperature. The mixture was then acidified by the addition of 3N aqueous hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 1:4 by volume mixture of ethyl acetate and hexane, to give 1.68 g of the title compound as slightly yellow crystals (yield 81%).

Workup

  1. customafter which the ethanol in the reaction mixture was removed by distillation under reduced pressure
  2. customThe remaining reaction solution
  3. temperaturewas heated
  4. temperatureunder reflux for 14 hours
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. washeluted with a 1:4 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ed8be36989a64b0583f4999ddd47b3ca
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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