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

HRID 842268Notes

Reaction equation

HRID 842268 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-40f96c4251b249d3a7ebcd63558d9a7d
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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