Sodium hydride → HCID 13248012, compound

HRID 1580978Notes

Reaction equation

HRID 1580978 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]2[CH2:17][NH:16][C:15](=[O:18])[CH:14]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29]Cl>CN(C)C=O>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29][C:14]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)[CH2:17][NH:16][C:15]1=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81740Veratryl chlorideHCID 13248011HCID 13248011, compound

Product 1

HCID 13248012HCID 13248012, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.3 g of a 50% suspension of sodium hydride in mineral oil is added to a solution of 29.3 g of ethyl 4-(3,4-dimethoxyphenyl)-2-oxo-3-pyrrolidinecarboxylate in 180 ml of anhydrous dimethylformamide at 0°-5°C with stirring. The resulting mixture is held at 0°-5°C with stirring for 30 minutes and then at room temperature for an additional one hour. To the mixture is added 20.5 g of 3,4-dimethoxybenzyl chloride at 0°-5°C, and the whole mixture is stirred at room temperature for one hour. The reaction mixture is then concentrated 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 anhydrous magnesium sulfate and concentrated under reduced pressure. The residual oil is crystallized with ethanol to give 34.1 g of ethyl 3-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxyphenyl)-2-oxo-3-pyrrolidinecarboxylate as white crystals, melting at 146°-149°C.

Workup

  1. customis held at 0°-5°C
  2. stirringwith stirring for 30 minutes
  3. stirringthe whole mixture is stirred at room temperature for one hour
  4. concentrationThe reaction mixture is then concentrated under reduced pressure
  5. additionWater is 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 anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residual oil is crystallized with ethanol

Sources & evidence

ORD record
ord-7773d9cbbdc14541bd32ccf07bf91470
Source dataset
uspto-grants-1976_01
Patent number
US03935217

Reaction notes

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