Trifluoroacetate → HCID 22047292, compound

HRID 656966Notes

Reaction equation

HRID 656966 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 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.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 18 h
  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-df121f51c50e4de58dab24b11ef690b1
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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