反応 #4492

反応方程式

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

溶媒

chloroform

反応条件

後処理

1. 1
   ろ過The mixture was filtered hot
2. 2
   濃縮the filtrate was concentrated in vacuo
3. 3
   洗浄A solution of the residue in ethyl acetate was successively washed with saturated aqueous sodium bicarbonate solution and water
4. 4
   乾燥dried over magnesium sulfate
5. 5
   その他The solvent was removed
6. 6
   その他the residue was recrystallized from ethanol

実験手順

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.

出典