Hydrochloric Acid → HCID 12181442, compound

HRID 1534388Notes

Reaction equation

HRID 1534388 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].I[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.Cl>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.O.C(#N)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3]#[C:2][CH2:1][OH:4])[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 707143-Iodopyridine

Product 1

HCID 12181442HCID 12181442, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Propynyl alcohol (2.1 g) was added dropwise to a stirred mixture of 3-iodopyridine (2.2 g), bis(triphenylphosphine)palladium chloride (0.1 g), triethylamine (1.4 ml), cuprous iodide (0.1 g) and acetonitrile (10 ml) and the mixture was stirred at ambient temperature for 30 minutes and the heated to 60° C. for 2 hours. The mixture was cooled to ambient temperature, poured into water (100 ml) and neutralised by adding dilute aqueous hydrochloric acid. The mixture was extracted with diethyl ether (2×100 ml) and the combined extracts were washed with water (100 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with methylene chloride to give 3-(3-pyridyl)prop-2-yn-1-yl alcohol (0.8 g), m.p. 99°-100° C.

Workup

  1. temperaturethe heated to 60° C. for 2 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionThe mixture was extracted with diethyl ether (2×100 ml)
  4. washthe combined extracts were washed with water (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride

Sources & evidence

ORD record
ord-bc33ea14cd5449448288ea8767836ee9
Source dataset
uspto-grants-1992_02
Patent number
US05089495

Reaction notes

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