Ethyl Acetate → HCID 67808707, compound

HRID 22485Notes

Reaction equation

HRID 22485 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:2]=1.C(OCC)(=O)C>[Pd].C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:2]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 135575516-(Pyridin-3-YL)hex-5-YN-1-OL

Product 1

HCID 67808707HCID 67808707, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-(3-Pyridyl)-1-hex-5-ynol (0.15 g, 0.86 mmol) was added to a stirred suspension of 10% palladium on charcoal (20 mg) in ethanol. The reaction was stirred at room temperature under hydrogen for 24 h. The mixture was filtered through celite and evaporated to give a clear oil. Column chromatography (flash silica gel; ethyl acetate) gave Z-6-(3-pyridyl)-1-hex-5-enol (70 mg, 46%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated
  3. customto give a clear oil

Sources & evidence

ORD record
ord-14b42dda1a0a43b6a9e6712d1e2c1bcf
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Reaction notes

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