Reaction #54591

ord-238e2c7868bf4c0ab667f4ccfcc35579

Reaction equation

O
water
ClC(Cl)Cl
Chloroform
O=C1NC(=O)c2ccccc21.[K]
potassium phthalimide
CCCC(Br)C(=O)OCC
ethyl-2-bromopentanoate
→
CCCC(C(=O)OCC)N1C(=O)c2ccccc2C1=O
ethyl α-phthalimidopentanoate

Reactants

O
water
ClC(Cl)Cl
Chloroform
O=C1NC(=O)c2ccccc21.[K]
potassium phthalimide
CCCC(Br)C(=O)OCC
ethyl-2-bromopentanoate

Reagents

None

Solvents

CN(C)C=O
DMF
CN(C)C=O
dimethylformamide

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe phases are separated
  2. 2
    Extractionthe aqueous phase is extracted with chloroform
  3. 3
    Extractionextracted with 0.1 N sodium hydroxide and with water
  4. 4
    DryingAfter drying over sodium sulfate
  5. 5
    Otherthe chloroform is removed

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04148998uspto-grants-1979_04