Phenylacetylene → HCID 10176527, compound

HRID 896475Notes

Reaction equation

HRID 896475 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.[Cu]I>[C:9]1([C:15]#[C:16][C:2]2[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 10176527HCID 10176527, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromofuraldehyde (1.0 g, 5.71 mmol, 1 eq), copper (I) iodide (0.163 g, 0.857 mmol, 0.15 eq), trans-dichlorobis(triphenylphosphine) palladium(II) (0.20 g, 0.287 mmol, 0.05 eq), and TEA (3.98 mL, 28.6 mmol, 5 eq) in THF (45 mL) is added dropwise phenyl acetylene (1.25 mL, 11.4 mmol, 2 eq). After 48 hr, the reaction appears complete. The reaction is filtered over a pad of celite, and the solvent is removed under reduced pressure. The reaction is purified by silica gel chromatography using a Biotage Flash 40M column (10% EtOAc/heptane) to give 5-phenylethynyl-furan-2-aldehyde as a yellow orange crystalline solid (0.765 g, 68.3%).

Workup

  1. filtrationThe reaction is filtered over a pad of celite
  2. customthe solvent is removed under reduced pressure
  3. customThe reaction is purified by silica gel chromatography

Sources & evidence

ORD record
ord-1cacf8b323cc45e58934304ed8f71738
Source dataset
uspto-grants-2005_07
Patent number
US06919359B2

Reaction notes

Loading…