Benzoyl chloride → 1-Benzoyl-5-propoxypyrrolidin-2-one
Reaction equation
C([Li])CCC.[CH2:6]([O:10][CH:11]1[NH:15][C:14](=[O:16])[CH2:13][CH2:12]1)[CH2:7][CH2:8]C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCC.O1CCCC1>[C:17]([N:15]1[CH:11]([O:10][CH2:6][CH2:7][CH3:8])[CH2:12][CH2:13][C:14]1=[O:16])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -60 °C
Procedure
17 cm3 of a 1.5M solution of n-butyllithium in n-hexane is added at -60° C. to a solution of 4 g of 5-(1-butyloxy) pyrrolidin-2-one in 90 cm3 of tetrahydrofuran. The whole is agitated for 15 minutes at -60° C. then, at this temperature, a solution of 3.58 g of benzoyl chloride in 25 cm3 of tetrahydrofuran is added. After allowing the temperature to return to the ambient, the solvent is evaporated under reduced pressure and the residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3) and 4 g of expected product is obtained. b.p. =200°-210° C. under 0.07 mbar.
Workup
- customthe solvent is evaporated under reduced pressure
- customthe residue is chromatographed on silica (eluent: ethyl acetate-n-hexane 1-3)
Sources & evidence
- ORD record
- ord-7101b1b1e27943ec842a3f40d161716e
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04948804
Reaction notes
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