Benzoyl chloride → 1-Benzoyl-5-propoxypyrrolidin-2-one

HRID 1709172Notes

Reaction equation

HRID 1709172 reaction equation
C([Li])CCC.[CH2:6]([O:9][CH:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)[CH2:7][CH3:8].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[C:16]([N:14]1[CH:10]([O:9][CH2:6][CH2:7][CH3:8])[CH2:11][CH2:12][C:13]1=[O:15])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 15696555HCID 15696555, compoundHCID 178418339Butyllithium

Product 1

HCID 30779361-Benzoyl-5-propoxypyrrolidin-2-oneYield 57.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

18.6 cm3 of a 1.5M solution of n-butyllithium in hexane is added to a solution of 4 g of 5-(1-propyloxy) pyrrolidin-2-one in tetrahydrofuran at -60° C., while maintaining the temperature between -55° C. and -60° C. After agitation for 15 minutes at -60° C. a solution of 3.93 g of benzoyl chloride in 20 cm3 of tetrahydrofuran is added at this temperature. After allowing the mixture to return to ambient temperature, the solvent is evaporated under reduced pressure. The residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3) and 4 g of the expected product is obtained. b.p. =200° C. under 0.1 mbar.

Workup

  1. temperaturewhile maintaining the temperature between -55° C. and -60° C
  2. customto return to ambient temperature
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3)

Sources & evidence

ORD record
ord-46eb0a1e764d4e6595c8c4707ff70392
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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