Acetic Anhydride → HCID 19978928, compound

HRID 1084642Notes

Reaction equation

HRID 1084642 reaction equation
[CH3:1][C:2]([N:10]1[CH2:14][C:13]([OH:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:22])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:23]([O:15][C:13]1[CH2:14][N:10]([C:2]([CH3:1])([CH3:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11](=[O:22])[C:12]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54692130HCID 54692130, compound

Product 1

HCID 19978928HCID 19978928, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 g (17 mmol) of 1-(α,α-dimethylbenzyl)-4-hydroxy-2-oxo-3-phenyl-3-pyrroline prepared by the method of Reference Example 13, was dissolved in a solution of 10 ml of acetic anhydride and 20 ml of pyridine, and the solution was stirred at room temperature for one day and night. Ice water was added to the reaction solution and extracted with ethyl acetate. The ethyl acetate layer was thoroughly washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from isopropyl ether to obtain 4.2 g (yield: 81%) of the desired compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was thoroughly washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-9c644508f21b4678957ebe993cb463d9
Source dataset
uspto-grants-1991_04
Patent number
US05006157

Reaction notes

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