2-Acetyl-6-(3-hydroxy-2-propynyl)pyridine → 2-Acetyl-6-(3-hydroxypropyl)-pyridine

HRID 53210Notes

Reaction equation

HRID 53210 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]#[C:12][OH:13])[N:5]=1)(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[N:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 190820102-Acetyl-6-(3-hydroxy-2-propynyl)pyridine

Product 1

HCID 190820072-Acetyl-6-(3-hydroxypropyl)-pyridineYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1.3 g of 2-acetyl-6-(3-hydroxy-2-propynyl)pyridine and 0.5 g of 10% Pd/C in 50 ml of ethyl acetate was hydrogenated at 50 psi (H2) overnight. The mixture was filtered and the filtrate was concentrated in vacuo to yield 1.1 g (84.6%) of 2-acetyl-6-(3-hydroxypropyl)-pyridine, as a yellow oil (crude).

Workup

  1. customwas hydrogenated at 50 psi (H2) overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3220137bd9a74e25a876712979ff80b5
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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