Reaktion #4492

Reaktionsgleichung

Methanol

5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione

acetic acid

→

5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered hot
2. 2
   Einengenthe filtrate was concentrated in vacuo
3. 3
   WaschenA solution of the residue in ethyl acetate was successively washed with saturated aqueous sodium bicarbonate solution and water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   SonstigeThe solvent was removed
6. 6
   Sonstigethe residue was recrystallized from ethanol

Vorschrift

A stirred mixture of 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (500 mg), 10% Pd-C (50% wet, 1.0 g) and acetic acid (50 ml) was hydrogenated at 70° C. and at atmospheric pressure for 3 hours. Methanol (20 ml) and chloroform (20 ml) were added to the mixture and the whole was heated at 60° C. for 5 minutes. The mixture was filtered hot and the filtrate was concentrated in vacuo. A solution of the residue in ethyl acetate was successively washed with saturated aqueous sodium bicarbonate solution and water, and dried over magnesium sulfate. The solvent was removed and the residue was recrystallized from ethanol to yield 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl}-2,4-thiazolidinedione (the same compound as that obtained in Example 12) as crystals (415 mg, 82.7%). m.p. 113°-114° C.

Quelle