Triethylamine → 3-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)furan-2(5H)-one

HRID 446794Notes

Reaction equation

HRID 446794 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:19][C:20](=O)[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:17])[O:18][CH2:19][C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 673017532-Oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate

Product 1

HCID 670750913-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)furan-2(5H)-oneYield 10.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate (1.8 g, 0.004 mol) in acetonitrile (50 mL) was added triethylamine (10 mL, 0.07 mol) under an inert atmosphere. The reaction mixture was then refluxed for 2 h, concentrated in vacuo, and the residue was dissolved in EtOAc (100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to yield the crude product. The crude material was purified via silica gel column chromatography to afford 3-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)furan-2(5H)-one (140 mg, 8%).

Workup

  1. temperatureThe reaction mixture was then refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (100 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield the crude product
  9. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-713e0dc980d94c18ab4821eb5e143f6e
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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