Propargyl alcohol → 3-(Pyridin-2-yl)prop-2-yn-1-ol

HRID 398020Notes

Reaction equation

HRID 398020 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:11])[C:9]#[CH:10]>[Cu]I.C(NCC)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:10]#[C:9][CH2:8][OH:11]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 79732-Bromopyridine

Product 1

HCID 34811473-(Pyridin-2-yl)prop-2-yn-1-olYield 77%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

The mixture that consists of 16.6 ml (173 mmol) of 2-bromopyridine, 21.6 ml of propargyl alcohol, 2.5 g of palladium-bis-triphenylphosphine-dichloride and 173 mg of copper(I) iodide is mixed with 510 ml of diethylamine and heated for 1.5 hours to 80° C. After filtration and removal of the solvent, the residue is purified by chromatography on fine silica gel with a gradient system that consists of n-hexane and ethyl acetate. 17.8 g (134 mmol, 77%) of the title compound is isolated as a colorless oil.

Workup

  1. temperatureheated for 1.5 hours to 80° C
  2. filtrationAfter filtration and removal of the solvent
  3. customthe residue is purified by chromatography on fine silica gel with a gradient system that

Sources & evidence

ORD record
ord-d28451f836ab49a793ad3f43adaff925
Source dataset
uspto-grants-2003_08
Patent number
US06610736B1

Reaction notes

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