Iodoethane → 1-Ethyl-4-phenyl-pyrrolidin-2-one

HRID 255912

Reaction equation

HRID 255912 reaction equation
[C:1]1([CH:7]2[CH2:11][NH:10][C:9](=[O:12])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:15](I)[CH3:16]>O1CCCC1>[CH2:15]([N:10]1[CH2:11][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]1=[O:12])[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1213974-Phenyl-2-pyrrolidinone

Product 1

HCID 133622481-Ethyl-4-phenyl-pyrrolidin-2-oneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-phenyl-pyrrolidin-2-one (24.2 g; 0.15 mole) and sodium hydride (80% oil suspension)(5.4 g; 0.18 mole) in tetrahydrofuran (150 ml) is refluxed for 2.5 hrs. After cooling, ethyl iodide (29 g; 0.185 mole) is added thereto, and the resulting material is refluxed for another 5 hrs. The solvent is then evaporated off; the residue is taken up into chloroform, washed with water, dried and distilled. B.p.(0.2 mm Hg)=124°-126° C. Yield: 57%.

Workup

  1. temperatureis refluxed for 2.5 hrs
  2. temperatureAfter cooling
  3. temperaturethe resulting material is refluxed for another 5 hrs
  4. customThe solvent is then evaporated off
  5. washwashed with water
  6. customdried
  7. distillationdistilled
  8. custom(0.2 mm Hg)=124°-126° C

Sources & evidence

ORD record
ord-2783fa82418d4d678848ed78ed9d78f7
Source dataset
uspto-grants-1987_10
Patent number
US04699918

Linked notes

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