Benzoyl chloride → 2-Pyrrolidinone, 1-benzoyl-5-(pentyloxy)-, (+-)-

HRID 1709176Notes

Reaction equation

HRID 1709176 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:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCCCCC.O1CCCC1>[C:18]([N:16]1[CH:12]([O:11][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:13][CH2:14][C:15]1=[O:17])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 156965585-Pentyloxy-pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 30779432-Pyrrolidinone, 1-benzoyl-5-(pentyloxy)-, (+-)-Yield 62.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

15.56 cm3 of a 1.5M solution of n-butyllithium in hexane is added at -60° 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 -60° C. and then under these conditions a solution of 3.28 g of benzoyl chloride in 20 cm3 of tetrahydrofuran is added. After allowing the temperature to return to ambient, the solvent is evaporated under reduced pressure. The residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3) and 4 g of sought product is obtained.

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. customThe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3)

Sources & evidence

ORD record
ord-a3a9f3c967d042f4890126d286b13e51
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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