Reacción #350778

Ecuación de reacción

sodium hydride

1-bromononane

2-(3,4-diethoxyphenyl)-4-(3-carboxy-4-methoxymethoxyphenyl)thiazole

→

2-(3,4-diethoxyphenyl)-4-(3-nonyloxycarbonyl-4-methoxymethoxyphenyl)thiazole

Rendimiento 43.8%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed by distillation
2. 2
   workup.ADDITIONTo the residue were added
3. 3
   Otro80 ml of dichloromethane and 30 ml of a 10% aqueous sodium hydroxide solution, and phase separation
4. 4
   LavadoThe dichloromethane portion was washed with 20 ml of a saturated aqueous sodium chloride solution
5. 5
   Otrodried
6. 6
   workup.DISTILLATIONsubjected to distillation
7. 7
   Otroto remove the solvent

Procedimiento

In 5 ml of dimethylformamide was dissolved 600 mg of 2-(3,4-diethoxyphenyl)-4-(3-carboxy-4-methoxymethoxyphenyl)thiazole. Thereto was added 56 mg of sodium hydride and 290 mg of 1-bromononane. The mixture was stirred at room temperature for 14 hours. The solvent was removed by distillation. To the residue were added 80 ml of dichloromethane and 30 ml of a 10% aqueous sodium hydroxide solution, and phase separation was conducted. The dichloromethane portion was washed with 20 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was subjected to silica gel column chromatography. There was obtained, from the dichloromethane layer, 340 mg of 2-(3,4-diethoxyphenyl)-4-(3-nonyloxycarbonyl-4-methoxymethoxyphenyl)thiazole as a colorless oily substance.

Fuente