Benzoyl chloride → 1-Benzoyl-5-(octyloxy)pyrrolidin-2-one

HRID 1709180Notes

Reaction equation

HRID 1709180 reaction equation
C([Li])CCC.[CH2:6]([O:14][CH:15]1[NH:19][C:18](=[O:20])[CH2:17][CH2:16]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCCCCC.O1CCCC1>[C:21]([N:19]1[CH:15]([O:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:16][CH2:17][C:18]1=[O:20])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 15696565HCID 15696565, compoundHCID 178418339Butyllithium

Product 1

HCID 30779561-Benzoyl-5-(octyloxy)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

16.5 cm3 of a 15% solution of butyllithium in hexane is added at -60° C. to 5.3 g of 5-n-octyloxy pyrrolidin-2-one in solution in 200 cm3 of tetrahydrofuran. After agitation for 20 minutes at -60° C., then, while maintaining these conditions, a solution of 3.5 g of benzoyl chloride in 50 cm3 of tetrahydrofuran is added. Agitation is continued while allowing to return to ambient temperature. After concentration and chromatography on silica (eluent: toluene-ethyl acetate 8-2), 4.2 g of the product sought is obtained.

Workup

  1. temperaturewhile maintaining these conditions
  2. customto return to ambient temperature
  3. concentrationAfter concentration and chromatography on silica (eluent: toluene-ethyl acetate 8-2), 4.2 g of the product
  4. customsought is obtained

Sources & evidence

ORD record
ord-132333b5d7f04286a9cbc2b70fd7d8f4
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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