Trifluoroacetate → HCID 22047292, compound

HRID 2233180Notes

Reaction equation

HRID 2233180 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si](C)(C)C)[C:9]([OH:18])=[CH:8][N:7]=1)(=[O:3])[CH3:2].FC(F)(F)C([O-])=O>N1C=CC=CC=1.[Cu]I>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]2[CH:12]=[CH:13][O:18][C:9]2=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 84468TrifluoroacetateHCID 57423119{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

Product 1

HCID 22047292HCID 22047292, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1049PyridineSolvent

Procedure

{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.

Workup

  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

Sources & evidence

ORD record
ord-065ff870a018479994eaaf97fb6548f6
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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