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

HRID 1709179Notes

Reaction equation

HRID 1709179 reaction equation
C([Li])CCC.[CH2:6]([O:13][CH:14]1[NH:18][C:17](=[O:19])[CH2:16][CH2:15]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCCCCC.O1CCCC1>[C:20]([N:18]1[CH:14]([O:13][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:15][CH2:16][C:17]1=[O:19])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 156965645-(n-Heptyloxy)-pyrrolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 30779551-Benzoyl-5-(heptyloxy)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

16.5 cm3 of a 15% solution butyllithium in hexane is added at -60° C. to 4.98 g of 5-n-heptyloxy pyrrolidin-2-one in solution in 100 cm3 of tetrahydrofuran. After 20 minutes of agitation at -60° C., 3.5 g of benzoyl chloride in 25 cm3 of tetra-hydrofuran is added at this temperature. Agitation is carried out for 4 hours, allowing the mixture to return to ambient temperature. After concentration at 40° C., the residue is taken up in water, extracted with ether and concentrated to dryness. The residue is chromatographed on silica (eluent: toluene-ethyl acetate 8-2) and 1.2 g of the product sought is obtained.

Workup

  1. waitAgitation is carried out for 4 hours
  2. customto return to ambient temperature
  3. concentrationAfter concentration at 40° C.
  4. extractionextracted with ether
  5. concentrationconcentrated to dryness
  6. customThe residue is chromatographed on silica (eluent: toluene-ethyl acetate 8-2) and 1.2 g of the product
  7. customsought is obtained

Sources & evidence

ORD record
ord-d4ff9a4894424e6e9df4a19b83daabed
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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