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

HRID 963315Notes

Reaction equation

HRID 963315 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.Cl[Pd]Cl>[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

7

Reactant 2

HCID 7859Propargyl alcoholHCID 112985782-Acetyl-6-bromopyridine

Product 1

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

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 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 (2×), 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 (2×), 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-463269b04ade418c92c87039ebf0645a
Source dataset
uspto-grants-1998_06
Patent number
US05763461

Reaction notes

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