4-Methoxybenzyl bromide → 5-Ethoxy-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one

HRID 1639043Notes

Reaction equation

HRID 1639043 reaction equation
[CH2:1]([O:3][CH:4]1[NH:8][C:7](=[O:9])[CH2:6][CH2:5]1)[CH3:2].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:8]2[CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][C:7]2=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 1650214-Methoxybenzyl bromideHCID 35805555-Ethoxy-2-pyrrolidinone

Product 1

HCID 30779585-Ethoxy-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-oneYield 71.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2.25 g of 5-ethoxy-pyrrolidin-2-one, 1.23 g of hydrated potassium hydroxide and 0.2 g of tetra-n-butylammonium bromide in 45 cm3 of tetrahydrofuran, there is added, without exceeding 30° C., a solution of 3.5 g of 4-methoxybenzyl bromide in 15 cm3 of tetrahydrofuran. After agitating for 1 hour at ambient temperature, filtering and evaporating the solvent under reduced pressure, the residue is taken up with water and extracted with ethyl acetate. The extracts are dried and the solvent is evaporated under reduced pressure. The residue is distilled at 245° C. under 0.2 mbar. 3.10 g of the expected product is obtained.

Workup

  1. additionis added
  2. customwithout exceeding 30° C.
  3. filtrationfiltering
  4. customevaporating the solvent under reduced pressure
  5. extractionextracted with ethyl acetate
  6. customThe extracts are dried
  7. customthe solvent is evaporated under reduced pressure
  8. distillationThe residue is distilled at 245° C. under 0.2 mbar

Sources & evidence

ORD record
ord-16711789884c4e4c9b2e354c854e55d8
Source dataset
uspto-grants-1989_11
Patent number
US04882350

Reaction notes

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