Benzyl Bromide → 1-Benzyl-5-(pentyloxy)pyrrolidin-2-one

HRID 1639039Notes

Reaction equation

HRID 1639039 reaction equation
[CH2:1]([O:6][CH:7]1[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:15]([N:11]1[CH:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:8][CH2:9][C:10]1=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 156965585-Pentyloxy-pyrrolidin-2-one

Product 1

HCID 30779621-Benzyl-5-(pentyloxy)pyrrolidin-2-oneYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4 g of 5-(n-pentyloxy)-pyrrolidin-2-one, 0.4 g of n-tetrabutylammonium bromide and 1.96 g of potassium hydroxide hydrated to 85% in 60 cm3 of tetrahydrofuran, there is added, without exceeding 30° C. a solution of 3.99 g of benzyl bromide in 20 cm3 of tetrahydrofuran. After agitating for 1 hour at ambient temperature, filtering, evaporating to dryness and chromatographing the residue on silica (eluent: ethyl acetate--n-hexane, 1--1), 4.5 g of the expected product is obtained.

Workup

  1. additionthere is added
  2. customwithout exceeding 30° C.
  3. filtrationfiltering
  4. customevaporating to dryness and chromatographing the residue on silica (eluent: ethyl acetate--n-hexane, 1--1)

Sources & evidence

ORD record
ord-4676a6e415ee4e74aa4a2c70b3b8e8b3
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

Loading…