Triethylamine → 1-Ethynyl-2-methoxybenzene

HRID 1814478Notes

Reaction equation

HRID 1814478 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C[Si]([C:14]#[CH:15])(C)C.C(N(CC)CC)C>CN(C)C=O>[C:14]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9])#[CH:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 68257o-Iodoanisole

Product 1

HCID 5829121-Ethynyl-2-methoxybenzeneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Iodoanisole (10.5 g) and trimethylsilylacetylene (10.3 g) were reacted in dimethylformamide (50 ml), in the presence of dichloro-bis-triphenylphosphine palladium (1.0 g), cuprous iodide (0.5 g) and triethylamine (15 ml) in nitrogen atmosphere at 50° C. for 12 hr. The resulting reaction solution was evaporated, and to the resulting residue was added ethyl acetate and water. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was dissolved in methanol (100 ml), a 5N aqueous solution of sodium hydroxide (20 ml) was added thereto, and then reacted at 60° C. for 1 hr. The reaction solution was evaporated, and to the resulting residue was added ether and water. The resulting ether layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a pale yellow oil (3.02 g, yield; 51%). (232-2) 2-[2-Methoxyphenyl)ethynyl]-5-methoxybenzaldehyde

Workup

  1. customThe resulting reaction solution
  2. customwas evaporated
  3. additionto the resulting residue was added ethyl acetate and water
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. dissolutionthe resulting residue was dissolved in methanol (100 ml)
  8. additiona 5N aqueous solution of sodium hydroxide (20 ml) was added
  9. customreacted at 60° C. for 1 hr
  10. customThe reaction solution was evaporated
  11. additionto the resulting residue was added ether and water
  12. washThe resulting ether layer was washed with water and brine
  13. dry with materialdried over magnesium sulfate
  14. customThe solvent was evaporated
  15. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-6c5fa405870946909d7f21b73f15bdf7
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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