Benzyl Bromide → 2-Pyrrolidinone, 5-(hexyloxy)-1-(phenylmethyl)-, (+-)-

HRID 1639040Notes

Reaction equation

HRID 1639040 reaction equation
[CH2:1]([O:7][CH:8]1[NH:12][C:11](=[O:13])[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:16]([N:12]1[CH:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:9][CH2:10][C:11]1=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 156965635-(n-Hexyloxy)-pyrrolidin-2-one

Product 1

HCID 30779632-Pyrrolidinone, 5-(hexyloxy)-1-(phenylmethyl)-, (+-)-Yield 70%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 3.5 g of 5-(n-hexyloxy)-pyrrolidin-2-one, 1.58 g of potassium hydroxide hydrated to 85% and 0.35 g of tetra-n-butylammonium bromide in 50 cm3 of tetrahydrofuran, there is added, at 20° C. to 25° C. a solution of 3.23 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, 1-2), 3.64 g of the expected product is obtained.

Workup

  1. filtrationfiltering
  2. customevaporating to dryness and chromatographing the residue on silica (eluent: ethyl acetate--n-hexane, 1-2)

Sources & evidence

ORD record
ord-0f05671b4b534c9eb2e3a7b466c04e34
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

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