Réaction #43629

Équation de réaction

Water

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

pyridine

trifluoromethanesulfonic anhydride

→

desired product

Rendement 84.9%

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

Rendement 84.9%

Solvants

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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)

Source