Réaction #350769

Équation de réaction

sodium boron hydride

2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-formylmethylphenyl)thiazole

→

2-(3,4-diethoxyphenyl)-4-[3-methoxycarbonyl-4-hydroxy-5-(2-hydroxyethyl)phenyl]-thiazole

Rendement 43.6%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGThe mixture was stirred at the same temperature for 30 minutes
3. 3
   AutreAfter the completion of a reaction
4. 4
   Autrethe solvent was removed by distillation
5. 5
   AutreThe residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane =4/1)
6. 6
   Autrerecrystallized from diethyl ether

Mode opératoire

111 mg of sodium boron hydride was added to a solution of 1.3 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-formylmethylphenyl)thiazole in 30 ml of methanol, with stirring under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. After the completion of a reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane =4/1) and recrystallized from diethyl ether to obtain 570 mg of 2-(3,4-diethoxyphenyl)-4-[3-methoxycarbonyl-4-hydroxy-5-(2-hydroxyethyl)phenyl]-thiazole.

Source