反応 #350782

反応方程式

methylamine

2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxy-methoxy-5-formylphenyl)thiazole

methanol

sodium boron hydride

→

2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-methylaminomethyl-phenyl)thiazole

反応条件

後処理

1. 1
   workup.STIRRINGwith stirring under ice-
2. 2
   温度cooling
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
4. 4
   その他The solvent was removed from the reaction mixture by distillation
5. 5
   workup.ADDITIONThe residue was mixed with 40 ml of ethyl acetate and 20 ml of water, and phase separation
6. 6
   洗浄The organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution
7. 7
   その他dried
8. 8
   workup.DISTILLATIONsubjected to distillation
9. 9
   その他to remove the solvent

実験手順

In 30 ml of methanol was dissolved 500 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxy-methoxy-5-formylphenyl)thiazole. Thereto was added 3 ml of a 30% methylamine solution. The mixture was stirred at room temperature for 14 hours and at 70° C. for 1 hour. Thereto was added 530 ml of sodium boron hydride with stirring under ice- cooling. The mixture was stirred at room temperature for 3 hours. The solvent was removed from the reaction mixture by distillation. The residue was mixed with 40 ml of ethyl acetate and 20 ml of water, and phase separation was conducted. The organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was subjected to silica gel chromatography (eluent: dichloromethane/methanol =49/1 by v/v). From the eluate was obtained 150 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-methylaminomethyl-phenyl)thiazole.

出典