Benzoyl chloride → 1-Benzoyl-5-(3-methylbutoxy)pyrrolidin-2-one

HRID 1709182Notes

Reaction equation

HRID 1709182 reaction equation
C([Li])CCC.[CH3:6][CH:7]([CH3:17])[CH2:8][CH2:9][O:10][CH:11]1[NH:15][C:14](=[O:16])[CH2:13][CH2:12]1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCCCCC.O1CCCC1>[C:18]([N:15]1[CH:11]([O:10][CH2:9][CH2:8][CH:7]([CH3:17])[CH3:6])[CH2:12][CH2:13][C:14]1=[O:16])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 15696560HCID 15696560, compoundHCID 178418339Butyllithium

Product 1

HCID 30779511-Benzoyl-5-(3-methylbutoxy)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

12.8 cm3 of a 1.5M solution of butyllithium in hexane is added at -70° C. to a solution of 3.3 g of 5-(3-methylbutoxy) pyrrolidin-2-one in 140 cm3 of tetrahydrofuran. The mixture is maintained for 20 minutes at this temperature, then a solution of 2.7 g of benzoyl chloride in 20 cm3 of tetrahydrofuran is added. The solution is returned to ambient temperature, concentrated to dryness under reduced pressure and chromatographed on silica (eluent: hexane-ethyl acetate 7-3) 3.5 g of expected product is obtained.

Workup

  1. temperatureThe mixture is maintained for 20 minutes at this temperature
  2. customis returned to ambient temperature
  3. concentrationconcentrated to dryness under reduced pressure
  4. customchromatographed on silica (eluent: hexane-ethyl acetate 7-3) 3.5 g of expected product
  5. customis obtained

Sources & evidence

ORD record
ord-597a06ec8dd34622b1ff78147ccf88ff
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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