反应 #1258902

反应方程式

diisobutylaluminium hydride toluene

ethyl 2-(t-butoxycarbonylamino)-1,3-thiazole-4-carboxylate

potassium sodium tartrate

→

[2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methanol

收率 73.0%

溶剂

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGthe whole was further stirred for 2 hours
2. 2
   过滤The mixture was filtered
3. 3
   其他the filtrate was partitioned between dichloromethane and water
4. 4
   其他The organic layer was separated
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   浓缩Concentration under reduced pressure

实验过程

A 1.0M diisobutylaluminium hydride toluene solution (142 ml) was added dropwise to a stirred solution of ethyl 2-(t-butoxycarbonylamino)-1,3-thiazole-4-carboxylate (14.9 g) in dichloromethane (250 ml) under cooling at −70° C. After the mixture was stirred successively at −78° C. for 2 hours and at 0° C. for 1 hour, an aqueous potassium sodium tartrate solution was added carefully to the mixture, and the whole was further stirred for 2 hours. The mixture was filtered using dichloromethane, and the filtrate was partitioned between dichloromethane and water. The organic layer was separated and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded a crude product of [2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methanol (9.2 g). The product thus obtained was treated with manganese dioxide (70 g) in dichloromethane (300 ml) with stirring at room temperature.

来源