Sodium ethoxide → HCID 14267835, compound

HRID 1650891Notes

Reaction equation

HRID 1650891 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:9][C:10](OCC)=[O:11])=[O:5])[CH3:2].[O-]CC.[Na+].[Na]>C1C=CC=CC=1.C(O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:8]2[CH2:7][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:10](=[O:11])[CH2:9]2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxide2×HCID 5360545SodiumHCID 14267833HCID 14267833, compound

Product 1

HCID 14267835HCID 14267835, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 702EthanolSolvent

Procedure

A solution of ethyl N-(b-ethoxycarbonylethyl)-N-(4-methoxyphenyl)glycinate (106.7 g, 0.345 mol) in dry benzene (400 mL) is added to a mixture of ethanolic sodium ethoxide in benzene (prepared by dissolving 13.1 g of sodium metal in 300 mL of ethanol and then the ethanolic sodium ethoxide solution is diluted with 500 mL of benzene) at room temperature over a period of 90 minutes. The mixture is heated at reflux for 30 minutes and then is cooled to room temperature. The solid is collected by filtration, and then is suspended in an ice-water mixture (1 L). The mixture, after being neutralized with 1 N hydrochloric acid, is extracted with diethyl ether (3×500 mL). The combined extracts are washed with water, dried over sodium sulfate, concentrated, and the residue is crystallized from n-hexane-diethyl ether to afford 1-(4-methoxyphenyl)-4-ethoxycarbonylpyrrolidine-3-one (87.4 g, 64%), mp 58°-60° C. 1H NMR (CDCl3) d 1.34 (3H, dt, CH2Me), 3.76 (3H, s, OMe), 3.75 (2H, dq, CH2Me), 4.14 (2H, s, 2-CH2), 4.12-4.39 (3H, m, H-4 and 5-CH2), 6.46 and 6.86 (each 2H, m, Ph).

Workup

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 30 minutes
  4. filtrationThe solid is collected by filtration
  5. extractionis extracted with diethyl ether (3×500 mL)
  6. washThe combined extracts are washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customthe residue is crystallized from n-hexane-diethyl ether

Sources & evidence

ORD record
ord-8988263fcea84c9485091f5389234a0b
Source dataset
uspto-grants-1990_05
Patent number
US04925939

Reaction notes

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