Reacción #43629

Ecuación de reacción

Water

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

pyridine

trifluoromethanesulfonic anhydride

→

desired product

Rendimiento 84.9%

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

Rendimiento 84.9%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred at room temperature for a further 4 h
2. 2
   Extracciónthe mixture was extracted three times with diethyl ether
3. 3
   Lavadothe combined organic extracts washed again with water
4. 4
   SecadoThe organic extracts were dried with magnesium sulphate
5. 5
   Otroevaporated
6. 6
   OtroThe residue was chromatographed on silica eluting with 0-10% methanol in dichloromethane

Procedimiento

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)

Fuente