Hydrochloric Acid → 2-(2-(2-Benzyloxyphenyl)ethyl)-2-ethoxycarbonylpentanoic acid

HRID 617584Notes

Reaction equation

HRID 617584 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([CH2:28][CH2:29][CH3:30])([C:23]([O:25]CC)=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:28][CH2:29][CH3:30])[C:23]([OH:25])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22618813Diethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-propylmalonate

Product 1

HCID 226188042-(2-(2-Benzyloxyphenyl)ethyl)-2-ethoxycarbonylpentanoic acidYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of diethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-propylmalonate (10 g) in ethanol (50 ml), a solution of potassium hydroxide (1.9 g) in ethanol (180 ml) was added and the mixture was refluxed under heating for 6.5 hours. Ethanol (45 ml) was added thereto and the mixture was stirred at room temperature for 4 days. The reaction mixture was poured into a dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; chloroform-methanol=12:1) to give the subject compound (5.7 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-ba729b748e3141bfb51bf486af32ab4e
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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