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

HRID 1709178Notes

Reaction equation

HRID 1709178 reaction equation
C([Li])CCC.[CH2:6]([O:12][CH:13]1[NH:17][C:16](=[O:18])[CH2:15][CH2:14]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCCCC.O1CCCC1>[C:19]([N:17]1[CH:13]([O:12][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:14][CH2:15][C:16]1=[O:18])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 156965635-(n-Hexyloxy)-pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 30779542-Pyrrolidinone, 1-benzoyl-5-(hexyloxy)-, (+-)-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

16 cm3 of a 1.6M solution of butyllithium in hexane is added at -70° C. to 4.5 g of 5-n-hexyloxy pyrrolidin-2-one in solution in 130 cm3 of anhydrous tetrahydrofuran. Agitation is carried out for 20 minutes at -70° C. and under the same conditions a solution of 3.4 g of benzoyl chloride in 20 cm3 of tetrahydrofuran is added. After allowing to return to ambient temperature and concentration under reduced pressure, the residue is chromatographed on silica (eluent: toluene-ethyl acetate 8-2). 3.3 g of the product sought is obtained.

Workup

  1. customto return to ambient temperature
  2. concentrationconcentration under reduced pressure
  3. customthe residue is chromatographed on silica (eluent: toluene-ethyl acetate 8-2)

Sources & evidence

ORD record
ord-f4103594b0de49c88cdc27a230d885ad
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

Loading…