3-Butyn-1-OL → HCID 15332557, compound

HRID 1440999Notes

Reaction equation

HRID 1440999 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1I.[CH2:10]([OH:14])[CH2:11][C:12]#[CH:13]>C(N(CC)CC)C.C(#N)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>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]#[C:12][CH2:11][CH2:10][OH:14]

Participants

7

Reactant 2

HCID 135663-Butyn-1-OLHCID 968642,4-Dichloro-1-iodobenzene

Product 1

HCID 15332557HCID 15332557, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere 97.2 g (0.356 mole) of 2,4-dichloroiodobenzene, 3.21 g (0.0046 mole) of bis(triphenylphosphine)palladium(II) chloride, and 0.8 g (0.0042 mole) of copper(I) iodide were suspended in 50 mL of triethylamine and 100 mL of acetonitrile. This mixture was cooled in an ice/water bath to 0°-5° C., and 24.6 g (0.356 mole) of 3-butyn-1-ol dispersed in 25 mL of acetonitrile was added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature at which it was stirred for approximately 16 hours. The solvent was evaporated from the reaction mixture under reduced pressure, leaving a brown oil as the residue. This oil was passed through a column of silica gel, eluting first with hexane and then with methylene chloride. Product-containing factions were combined, and the solvent was evaporated under reduced pressure, leaving 4-(2,4-dichlorophenyl)-3-butyn-1-ol as the residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThis mixture was cooled in an ice/water bath to 0°-5° C.
  2. additionwas added dropwise
  3. additionUpon completion of addition
  4. customThe solvent was evaporated from the reaction mixture under reduced pressure
  5. customleaving a brown oil as the residue
  6. washeluting first with hexane
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0271a6f51e5848caa07baa9a36db58d4
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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