Methanol → HCID 19390069, compound

HRID 1757164Notes

Reaction equation

HRID 1757164 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:17][OH:18]>C1C=CC=CC=1>[CH3:17][O:18][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][N:14]1[CH2:15][CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12][C:13]1=[O:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 11775680HCID 11775680, compound

Product 1

HCID 19390069HCID 19390069, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

30 g (0.136M) of the pyrrolidone (9) was treated with Triton B (60 ml of a 40% methanol solution in 400 ml of benzene. Benzene was distilled off in vacuo, and 400 ml of benzene was again added to the residue. This procedure was repeated three times, and 25.31 g of 3,4-dimethoxybenzyl chloride was added thereto at room temperature. The mixture was stirred at 60° C. for 6 hr, and water was added to the reaction mixture. The resultant organic phase was separated and washed twice with water and once with a saturated saline solution. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off in vacuo. The residue was recrystallized from ethanol to prepare 41.54 g (yield: 82%) of the intended product.

Workup

  1. distillationBenzene was distilled off in vacuo, and 400 ml of benzene
  2. additionwas again added to the residue
  3. additionwas added
  4. customat room temperature
  5. additionwater was added to the reaction mixture
  6. customThe resultant organic phase was separated
  7. washwashed twice with water and once with a saturated saline solution
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off in vacuo
  10. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ef22e75559f64885bccda6d0fc128d03
Source dataset
uspto-grants-1995_08
Patent number
US05444083

Reaction notes

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