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

HRID 1709183Notes

Reaction equation

HRID 1709183 reaction equation
C([Li])CCC.[CH3:6][CH:7]([O:11][CH:12]1[NH:16][C:15](=[O:17])[CH2:14][CH2:13]1)[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][CH:7]([CH2:8][CH2:9][CH3:10])[CH3:6])[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 156965595-(2-Pentyloxy) pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 30779502-Pyrrolidinone, 1-benzoyl-2-(1-methylbutoxy)-, (+-)-Yield 65.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

12.4 cm3 of a 1.5M solution of butyllithium in hexane is added at -70° C. to a solution of 3.2 g of 5-(2-pentyloxy) pyrrolidin-2-one in 130 cm3 of tetrahydrofuran. The mixture is maintained at this temperature for 20 minutes, then a solution of 2.62 g of benzoyl chloride in 20 cm3 of tetrahydrofuran is added. The solution is returned to ambient temperature, concentrated and chromatographed on silica (eluent: hexane-ethyl acetate 7-3). 3.35 g of expected product is obtained.

Workup

  1. temperatureThe mixture is maintained at this temperature for 20 minutes
  2. customis returned to ambient temperature
  3. concentrationconcentrated
  4. customchromatographed on silica (eluent: hexane-ethyl acetate 7-3)

Sources & evidence

ORD record
ord-8bc34dceedb842cc9093def3fe0b7fdc
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

Loading…