Water → 4-[1,1-Dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile

HRID 1073880Notes

Reaction equation

HRID 1073880 reaction equation
[CH3:1][C:2]([CH3:14])([O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[C:3]#[CH:4].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.O.C(OCC)(=O)C>C(NCC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]([CH3:14])([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=1)[C:3]#[C:4][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2211262-IodopyridineHCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

Product 1

HCID 157329624-[1,1-Dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrileYield 88.2%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

53 mg of copper(I) iodide, 293 mg of triphenylphosphine and 99 mg of palladium(II) chloride were dissolved in 320 ml of diethylamine. 10.4 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile and 11.5 g of 2-iodopyridine were added and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 days. Water and ethyl acetate were added and the organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and then ethyl acetate/petroleum ether (1:2) for the elution to give 12.98 g of 4-[1,1-dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile in the form of an oil.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washethyl acetate/petroleum ether (1:2) for the elution

Sources & evidence

ORD record
ord-0c610147154c49018b3d7e6133960f93
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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