تفاعل #43629

معادلة التفاعل

Water

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

pyridine

trifluoromethanesulfonic anhydride

→

desired product

المردود 84.9%

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

المردود 84.9%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر