Water → 4-(Pyridin-3-yl)but-3-yn-1-ol

HRID 22484

Reaction equation

HRID 22484 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11].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:11]#[C:10][CH2:9][CH2:8][OH:12])[CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 122863-BromopyridineHCID 135663-Butyn-1-OL

Product 1

HCID 105829174-(Pyridin-3-yl)but-3-yn-1-olYield 12.3%

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 (3.75 g, 23.8 mmol), 3-butyn-1-ol (2.0 g, 28.5 mmol) and triethylamine (12 ml) in anhydrous DCM 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 product extracted into DCM. The combined organics were dried over anhydrous potassium carbonate, filtered and evaporated to give a brown oil. Column chromatography (flash silica gel, ethyl acetate) gave 4-(3-pyridyl)-1-but-3-ynol (0.43 g, 12%) as a colourless oil.

Workup

  1. temperatureThe mixture was refluxed for 20 h under argon
  2. temperatureAfter cooling
  3. extractionthe product extracted into DCM
  4. dry with materialThe combined organics were dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown oil

Sources & evidence

ORD record
ord-916c019ae2404726a039426cd3dd02e7
Source dataset
uspto-grants-1995_06
Patent number
US05428168

Linked notes

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