反应 #43629

反应方程式

Water

3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-1-propanol

pyridine

trifluoromethanesulfonic anhydride

→

desired product

收率 84.9%

7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2,3-dihydro-5(1H)-indolizinone

收率 84.9%

溶剂

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGstirred at room temperature for a further 4 h
2. 2
   萃取the mixture was extracted three times with diethyl ether
3. 3
   洗涤the combined organic extracts washed again with water
4. 4
   干燥The organic extracts were dried with magnesium sulphate
5. 5
   其他evaporated
6. 6
   其他The residue was chromatographed on silica eluting with 0-10% methanol in dichloromethane

实验过程

A solution of 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-1-propanol (5.16 g, 16.59 mmol) in dichloromethane (250 ml) was treated with pyridine (2.94 ml, 36.47 mmol) and trifluoromethanesulfonic anhydride (3.1 ml, 19.88 mmol) and stirred at room temperature for 10 min before being treated with tetrabutylammonium iodide (30.61 g, 82.95 mmol) and stirred at room temperature for a further 4 h. Water was then added and the mixture was extracted three times with diethyl ether and the combined organic extracts washed again with water. The organic extracts were dried with magnesium sulphate and evaporated. The residue was chromatographed on silica eluting with 0-10% methanol in dichloromethane to give the desired product (3.93 g, 14.09 mmol)

来源