Reaktion #744148

Reaktionsgleichung

{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

trifluoroacetate

→

Furo[2,3-c]pyridin-5-ylmethyl Acetate

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen heated
2. 2
   Temperaturunder reflux for 18 h
3. 3
   Temperaturto cool
4. 4
   Sonstigeevaporated to dryness
5. 5
   Sonstigethe residue partitioned between ethyl acetate and water
6. 6
   FiltrationThis mixture was filtered through kieselguhr
7. 7
   Sonstigeto remove copper residues
8. 8
   SonstigeThe organic layer was separated from the filtrate
9. 9
   Sonstigedried
10. 10
    Sonstigechromatographed on silica gel
11. 11
    Wascheneluting with a gradient of 10-60% ethyl acetate in 40-60° C. petroleum ether

Vorschrift

{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate, trifluoroacetate) (10 g, 22 mmol) was dissolved in pyridine (200 ml) and treated with copper(I) iodide (5.2 g, 27 mmol) then heated under reflux for 18 h. The mixture was allowed to cool, evaporated to dryness and the residue partitioned between ethyl acetate and water. This mixture was filtered through kieselguhr to remove copper residues. The organic layer was separated from the filtrate, dried and chromatographed on silica gel, eluting with a gradient of 10-60% ethyl acetate in 40-60° C. petroleum ether. This gave furo[2,3-c]pyridin-5-ylmethyl acetate (1.15 g, 27%) and a less polar product [2-(trimethylsilyl)furo[2,3-c]pyridin-5-yl]methyl acetate (1.3 g, 23%) as oils.

Quelle