Benzoyl chloride → 1-Benzoyl-5-[(propan-2-yl)oxy]pyrrolidin-2-one

HRID 1709173Notes

Reaction equation

HRID 1709173 reaction equation
C([Li])CCC.[CH:6]([O:9][CH:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)([CH3:8])[CH3:7].[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][CH:6]([CH3:8])[CH3:7])[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 15696556HCID 15696556, compoundHCID 178418339Butyllithium

Product 1

HCID 30779371-Benzoyl-5-[(propan-2-yl)oxy]pyrrolidin-2-oneYield 64.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

11.7 cm3 of a 1.6M solution of n-butyllithium in hexane is added at -70° C. to a solution of 2.5 g of 5-isopropyloxy pyrrolidin-2-one in 60 cm3 of tetrahydrofuran, while maintaining the temperature between -70° C. and -65° C. Agitation is carried out for 30 minutes under these conditions then a solution of 2.46 g of benzoyl chloride in 8 cm3 of tetrahydrofuran is added, maintaining the temperature between -65° C. and -70° C. The temperature is allowed to return to the ambient over 2 hours. After evaporation to dryness and then chromatography on silica (eluent: ethyl acetate-n-hexane 1-3), 2.78 g of the product sought is obtained.

Workup

  1. temperaturewhile maintaining the temperature between -70° C. and -65° C
  2. temperaturemaintaining the temperature between -65° C. and -70° C
  3. waitto return to the ambient over 2 hours
  4. customAfter evaporation to dryness

Sources & evidence

ORD record
ord-1924892b22674609bdac6f67d72ecd3f
Source dataset
uspto-grants-1990_08
Patent number
US04948804

Reaction notes

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