Water → Ethyl alpha-phthalimidopentanoate

HRID 26313

Reaction equation

HRID 26313 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH2:13]([O:15][C:16](=[O:22])[CH:17](Br)[CH2:18][CH2:19][CH3:20])[CH3:14].C(Cl)(Cl)Cl.O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH:17]([CH2:18][CH2:19][CH3:20])[C:16]([O:15][CH2:13][CH3:14])=[O:22])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 79071Ethyl 2-bromovalerateHCID 24194345Phthalimide potassium salt

Product 1

HCID 13791337Ethyl alpha-phthalimidopentanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of potassium phthalimide (0.1 mole) in about 50 ml of dimethylformamide (DMF) is added 1 equivalent of ethyl-2-bromopentanoate. The temperature is maintained at about 60° C. for 10 minutes. Chloroform is added to the cooled DMF solution and the mixture is poured into water. The phases are separated and the aqueous phase is extracted with chloroform. The chloroform extracts are combined, extracted with 0.1 N sodium hydroxide and with water. After drying over sodium sulfate, the chloroform is removed to give ethyl α-phthalimidopentanoate.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with chloroform
  3. extractionextracted with 0.1 N sodium hydroxide and with water
  4. dry with materialAfter drying over sodium sulfate
  5. customthe chloroform is removed

Sources & evidence

ORD record
ord-238e2c7868bf4c0ab667f4ccfcc35579
Source dataset
uspto-grants-1979_04
Patent number
US04148998

Linked notes

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