Phenylacetylene → HCID 54213497, compound

HRID 1648719Notes

Reaction equation

HRID 1648719 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][CH2:6][CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10].[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(N(CC)CC)C.[Pd].[Cu]I>[C:16]1([C:22]#[C:23][C:2]2[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=2)[O:5][CH2:6][CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 20481569HCID 20481569, compound

Product 1

HCID 54213497HCID 54213497, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 15 g (0.06 mole) of 1-(3-bromophenoxy)-2-diethylaminoethane and 6.12 g (0.06 mole) of phenylacetylene in 150 ml of triethylamine are added, under nitrogen, 420 mg of the palladium complex PdCl2 [P(C6H5)3 ]2 and 228 mg of copper (I) iodide. This reaction mixture is refluxed for 24 hours, then concentrated, and the residue is taken up in water. After extraction with 200 ml of ether, the combined ethereal phases are washed 4 times with water, dried, and evaporated to dryness. The crude product is chromatographed on silica gel and then distilled, affording 13.1 g (75%) of 1-(3-phenylethynylphenoxy)-2-diethylaminoethane with a boiling point of 150°-160° C./0.02 mb and a refractive index of nD25 :1.5858.

Workup

  1. temperatureThis reaction mixture is refluxed for 24 hours
  2. concentrationconcentrated
  3. extractionAfter extraction with 200 ml of ether
  4. washthe combined ethereal phases are washed 4 times with water
  5. customdried
  6. customevaporated to dryness
  7. customThe crude product is chromatographed on silica gel
  8. distillationdistilled

Sources & evidence

ORD record
ord-56c1592a92df443e97525312c28db416
Source dataset
uspto-grants-1983_11
Patent number
US04412856

Reaction notes

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