Pyridine → 1-Ethyl-4-benzyloxypyrrolidin-2-one

HRID 46429Notes

Reaction equation

HRID 46429 reaction equation
C(N1CC(O)CC1=O)C.N1C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1.[CH2:25]([N:27]1[CH2:31][CH:30]([O:32][C:33](=O)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:29][C:28]1=[O:41])[CH3:26]>C(OCC)(=O)C.O>[CH2:25]([N:27]1[CH2:31][CH:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:29][C:28]1=[O:41])[CH3:26]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 203870511-Ethyl-4-benzoyloxypyrrolidin-2-oneHCID 203870561-Ethyl-4-hydroxypyrrolidin-2-one

Product 1

HCID 203870581-Ethyl-4-benzyloxypyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Three g. 1-ethyl-4-hydroxypyrrolidin-2-one are dissolved in 30 ml. anhydrous pyridine and 2.7 ml. benzoyl chloride are added thereto. The reaction mixture is stirred overnight at ambient temperature, then it is poured into water containing 20 ml. concentrated sulphuric acid and extracted with ethyl acetate. The organic phases are collected, washed with a saturated aqueous solution of ammonium sulphate, evaporated to dryness and separated by chromatography to give 4.8 g. 1-ethyl-4-benzoyloxypyrrolidin-2-one; m.p. 53°-54° C.; Rf=0.27 (silica gel; eluant ethyl acetate).

Workup

  1. extractionconcentrated sulphuric acid and extracted with ethyl acetate
  2. customThe organic phases are collected
  3. washwashed with a saturated aqueous solution of ammonium sulphate
  4. customevaporated to dryness
  5. customseparated by chromatography
  6. customto give 4.8 g

Sources & evidence

ORD record
ord-5b7a6bbe0148453d8b28f9b5776e460e
Source dataset
uspto-grants-1979_11
Patent number
US04173569

Reaction notes

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