Water → 5-(3-Pyridinyl)-4-pentyn-1-ol

HRID 1463367Notes

Reaction equation

HRID 1463367 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:13])[CH2:9][CH2:10][C:11]#[CH:12].C(N(CC)CC)C.O>C(Cl)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.[Cu]I.C(OCC)(=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:12]#[C:11][CH2:10][CH2:9][CH2:8][OH:13])[CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 122863-BromopyridineHCID 793464-Pentyn-1-ol

Product 1

HCID 107970615-(3-Pyridinyl)-4-pentyn-1-olYield 8.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-bromopyridine (4.09 g, 26 mmol), 4-pentyn-1-ol (2.58 g, 31 mmol) and triethylamine (12 ml) in anhydrous DCM (20 ml) was added bis(triphenylphosphine)-palladium dichloride (0.05 g, 0.07 mmol) and copper(I) iodide (0.05 g, 0.26 mmol). The mixture was refluxed for 20 h under argon. After cooling, water (20 ml) was added and the products extracted into DCM. The combined organic extracts were washed with saturated potassium carbonate (50 ml) dried over anhydrous magnesium sulphate, filtered and evaporated to provide a brown oil. Column chromatography (flash silica gel, ethyl acetate) gave 5-(3-pyridyl)-1-pent-4-ynol (0.37 g, 7%) as a colourless oil.

Workup

  1. temperatureThe mixture was refluxed for 20 h under argon
  2. temperatureAfter cooling
  3. extractionthe products extracted into DCM
  4. washThe combined organic extracts were washed with saturated potassium carbonate (50 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto provide a brown oil

Sources & evidence

ORD record
ord-dd8e25b09a6748ec91bfe97082ad0071
Source dataset
uspto-grants-1994_04
Patent number
US05300524

Reaction notes

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