Reaktion #43629

Reaktionsgleichung

Water

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

pyridine

trifluoromethanesulfonic anhydride

→

desired product

Ausbeute 84.9%

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

Ausbeute 84.9%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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)

Quelle