Propargyl alcohol → HCID 12181442, compound

HRID 584166Notes

Reaction equation

HRID 584166 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:11])[C:9]#[CH:10]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:10]#[C:9][CH2:8][OH:11])[CH:3]=1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 122863-Bromopyridine

Product 1

HCID 12181442HCID 12181442, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 3-bromopyridine (6.25 ml), propargyl alcohol (4.9 ml), bis(triphenylphosphine)palladium(II) chloride (0.45 g) and copper iodide (125 mg) in triethylamine (100 ml) was stirred under reflux for 1.5 hours. After being cooled at room temperature, the reaction mixture was filtered and the insoluble material on the filter was washed with ethyl acetate (about 200 ml). The filtrate and the washing were combined and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate as eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give 3-(3-pyridyl)-2-propyn-1-ol (7.9 g) as brownish crystals.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. filtrationthe reaction mixture was filtered
  3. washthe insoluble material on the filter was washed with ethyl acetate (about 200 ml)
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate as eluent
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-891dab3a0d36455fab757352cf26576e
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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