Реакция #43629

Уравнение реакции

Water

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

pyridine

trifluoromethanesulfonic anhydride

→

desired product

Выход 84.9%

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

Выход 84.9%

Растворители

dichloromethane

Условия реакции

Обработка

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

Методика

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)

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