Benzyl Bromide → 1-Benzyl-5-propoxypyrrolidin-2-one

HRID 1639036Notes

Reaction equation

HRID 1639036 reaction equation
[CH2:1]([O:4][CH:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1)[CH2:2][CH3:3].[OH-].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[CH2:13]([N:9]1[CH:5]([O:4][CH2:1][CH2:2][CH3:3])[CH2:6][CH2:7][C:8]1=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 15696555HCID 15696555, compound

Product 1

HCID 30779591-Benzyl-5-propoxypyrrolidin-2-oneYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4 g of 5-(n-propyloxy)-pyrrolidin-2-one, 0.4 g of n-tetrabutylammonium bromide and 2.34 g of potassium hydroxide hydrated to 85% in 70 cm3 of tetrahydrofuran, there is added a solution of 4.78 g of benzyl bromide in 25 cm3 of tetrahydrofuran, operating at between 20° C. and 30° C. After agitating for 1 hour, filtering and then evaporating under reduced pressure, the residue is chromatographed on silica, (eluent: ethyl acetate--n-hexane, 1--1). 4 g of the expected product is obtained.

Workup

  1. customoperating at between 20° C. and 30° C
  2. filtrationfiltering
  3. customevaporating under reduced pressure
  4. customthe residue is chromatographed on silica, (eluent: ethyl acetate--n-hexane, 1--1)

Sources & evidence

ORD record
ord-452bdca9e98a4fd3ae222ca194617d99
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

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