Carbon Dioxide → 1-(4-Methoxyphenyl)pyrrolidin-3-one

HRID 1650892Notes

Reaction equation

HRID 1650892 reaction equation
C(OC([CH:6]1[CH2:10][N:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:8][C:7]1=[O:19])=O)C.C(=O)=O.C(=O)([O-])[O-].[K+].[K+]>Cl>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([N:9]2[CH2:10][CH2:6][C:7](=[O:19])[CH2:8]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 14267835HCID 14267835, compound

Product 1

HCID 142678391-(4-Methoxyphenyl)pyrrolidin-3-oneYield 74.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-ethoxycarbonyl-1-(4-methoxyphenyl)pyrrolidine-3-one (10.53 g, 0.04 mol) in 6N hydrochloric acid (120 mL) is heated at 100° C. (bath temperature) until evolution of carbon dioxide ceases (about 1 hour). The mixture is cooled in an ice-bath, neutralized with potassium carbonate, and then is extracted with diethyl ether (4×200 mL). The combined extracts are washed with water, dried over sodium sulfate, concentrated, and then the residue is crystallized from diethyl ether-n-hexane to give 1-(4-methoxyphenyl)pyrrolidine-3-one (5.68 g, 67%), mp 104°-105° C. 1H NMR (CDCl3) d 2.68 (2H, t, 5-CH2), 3.61 (2H, t, 4-CH2), 3.63 (2H, s, 2-CH2), 3.77 (3H, s, OMe), 6.63 and 6.89 (each 2H, d, Ph).

Workup

  1. temperatureThe mixture is cooled in an ice-bath
  2. extractionis extracted with diethyl ether (4×200 mL)
  3. washThe combined extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is crystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-259adf8cd2744d428eff433a5030686d
Source dataset
uspto-grants-1990_05
Patent number
US04925939

Reaction notes

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