Veratryl chloride → Ethyl 3-(3,4-dimethoxybenzyl)-4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylate

HRID 1580979

Reaction equation

HRID 1580979 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[CH2:14][NH:13][C:12](=[O:15])[CH:11]3[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][C:3]=2[O:2]1.[Na].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:27]Cl>C(O)C>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:27][C:11]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[CH2:14][NH:13][C:12]1=[O:15]

Participants

5

Reactant 3

HCID 81740Veratryl chlorideHCID 5360545SodiumHCID 21560852Ethyl 4-(2H-1,3-benzodioxol-5-yl)-2-oxopyrrolidine-3-carboxylate

Product 1

HCID 13248014Ethyl 3-(3,4-dimethoxybenzyl)-4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylateYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 9.9 g of ethyl 4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylate in 40 ml of absolute ethanol is added to a solution of 0.9 g of sodium in 50 ml of absolute ethanol at room temperature with stirring. The stirring is continued for one hour. To the mixture is added 8 g of 3,4-dimethoxybenzyl chloride. The resulting mixture is held at room temperature with stirring for one hour and then refluxed for an additional two hours. The ethanol is then removed under reduced pressure, water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from ethanol to give 11.5 g of ethyl 3-(3,4-dimethoxybenzyl)-4-(3,4-methylenedioxyphenyl)-2-oxo-3-pyrrolidinecarboxylate, melting at 167°-168°C.

Workup

  1. customis held at room temperature
  2. stirringwith stirring for one hour
  3. temperaturerefluxed for an additional two hours
  4. customThe ethanol is then removed under reduced pressure, water
  5. additionis added to the residue
  6. extractionthe aqueous mixture is extracted with ethyl acetate
  7. washThe extract is washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-fee57a492982478d9ff2e795bc7d1618
Source dataset
uspto-grants-1976_01
Patent number
US03935217

Linked notes

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