反应详情

{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 hrs. 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.

1. temperaturethen heated
2. temperatureunder reflux for 18 hrs
3. temperatureto cool
4. customevaporated to dryness
5. customthe residue partitioned between ethyl acetate and water
6. filtrationThis mixture was filtered through kieselguhr
7. customto remove copper residues
8. customThe organic layer was separated from the filtrate
9. customdried
10. customchromatographed on silica gel
11. washeluting with a gradient of 10-60% ethyl acetate in 40-60° C. petroleum ether