Triphenylphosphine → HCID 20481559, compound

HRID 1648723Notes

Reaction equation

HRID 1648723 reaction equation
O[C:2]([CH3:20])(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:7][CH:6]=1.I[C:22]1[S:23]C=C[CH:26]=1.[OH-].[K+].P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(N(CC)CC)C.CCOCC.[Pd].[Cu]I>[S:23]1[CH:22]=[CH:26][CH:20]=[C:2]1[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[CH:9][CH:10]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 189212-IodothiopheneHCID 20481568HCID 20481568, compound

Product 1

HCID 20481559HCID 20481559, compoundYield 75.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 11.07 g (0.04 mole) of 1-(3-hydroxy-3-methyl-1-butyn-1-yl)-4-(2-diethylaminoethoxy)benzene and 8.4 g (0.04 mole) of 2-iodothiophene in 135 ml of triethylamine are added, under nitrogen, 4.95 g of pulverised potassium hydroxide. Then 310 mg of the palladium complex PdCl2 [P(C6H5)3 ]2 and 180 ml of copper(I) iodide are added and the reaction mixture is stirred for 20 hours at boiling temperature. The reaction mixture is taken up in 250 ml of ether and the solution is washed 3 times with 100 ml of water and once with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue is chromatographed on silica gel with 96% of ether/4% of methanol (saturated with NH3), affording 9 g (75%) of 1-[4-(2-thienylethynyl)phenoxy]-2-diethylaminoethane in the form of a colourless oil with a refractive index of nD30 :1.6170.

Workup

  1. washthe solution is washed 3 times with 100 ml of water
  2. dry with materialonce with saturated sodium chloride solution, dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe residue is chromatographed on silica gel with 96% of ether/4% of methanol (saturated with NH3)

Sources & evidence

ORD record
ord-0c84fd0fa886455a803e7dd62f215983
Source dataset
uspto-grants-1983_11
Patent number
US04412856

Reaction notes

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