Propargyl alcohol → 2-Acetyl-6-(3-hydroxy-2-propynyl)pyridine

HRID 53209Notes

Reaction equation

HRID 53209 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[N:5]=1)(=[O:3])[CH3:2].[CH2:11]([OH:14])[C:12]#[CH:13]>C(N(CC)CC)C.O.[Cu]I>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:13][C:12]#[C:11][OH:14])[N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 190820102-Acetyl-6-(3-hydroxy-2-propynyl)pyridineYield 50%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 3 g (15.1 mmol) of 2-acetyl-6-bromopyridine, 0.89 g (15.9 mmol) of propargyl alcohol, 0.078 g of CuI, 300 mg of PdCl2 (P(Ph)3)2 in 60 ml of triethylamine was stirred under nitrogen at room temperature for 6 h. The mixture was diluted with water, extracted with ether, and the organic layer was washed with water (2x), brine, and dried over magnesium sulfate. The organic solution was concentrated in vacuo and the residue was purified by MPLC (silica gel 60, hexane/ethyl acetate, 1:1) to afford 1.3 g (50%) of 2-acetyl-6-(3-hydroxy-2-propynyl)pyridine, as a solid product.

Workup

  1. extractionextracted with ether
  2. washthe organic layer was washed with water (2x), brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic solution was concentrated in vacuo
  5. customthe residue was purified by MPLC (silica gel 60, hexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-668fa649768f42729a13b928e0334dce
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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