p-Anisoyl chloride → 2-Pyrrolidinone, 1-(4-methoxybenzoyl)-5-(pentyloxy)-, (+-)-

HRID 1709177Notes

Reaction equation

HRID 1709177 reaction equation
C([Li])CCC.[CH2:6]([O:11][CH:12]1[NH:16][C:15](=[O:17])[CH2:14][CH2:13]1)[CH2:7][CH2:8][CH2:9][CH3:10].[C:18](Cl)(=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CCCCCC.O1CCCC1.C1(C)C=CC=CC=1>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:16]2[CH:12]([O:11][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:13][CH2:14][C:15]2=[O:17])=[O:27])=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 156965585-Pentyloxy-pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 30779452-Pyrrolidinone, 1-(4-methoxybenzoyl)-5-(pentyloxy)-, (+-)-Yield 71.6%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

15.57 cm3 of a 1.5M solution of n-butyllithium in n-hexane is added at -70° C. to a solution of 4 g of 5-(1-pentyloxy) pyrrolidin-2-one in 80 cm3 of tetrahydrofuran. Agitation is carried out for 15 minutes at -70° C. then while maintaining this temperature, a solution of 3.98 g of para-anisoyl chloride at 58% in toluene is added. After allowing to return to ambient tempera-ture and evaporating under reduced pressure, the residue is chromatographed on silica (eluent: n-hexane-ethyl acetate 2-1). 5.1 g of sought product is obtained.

Workup

  1. temperaturewhile maintaining this temperature
  2. customevaporating under reduced pressure
  3. customthe residue is chromatographed on silica (eluent: n-hexane-ethyl acetate 2-1)

Sources & evidence

ORD record
ord-605c5aafa731402cb6fb8735426a3bf8
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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