Sodium Hydroxide → HCID 21835245, compound

HRID 1741273Notes

Reaction equation

HRID 1741273 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[OH-].[Na+].[CH2:11]([OH:16])[CH2:12][CH2:13][C:14]#[CH:15]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I.C(OCC)(=O)C>[N:6]1[CH:7]=[CH:8][C:3]([C:15]#[C:14][CH2:13][CH2:12][CH2:11][OH:16])=[CH:4][CH:5]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 793464-Pentyn-1-olHCID 881004-Bromopyridinium chloride

Product 1

HCID 21835245HCID 21835245, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromopyridine hydrochloride (5 g, 0.031 mol) was partitioned between 2N NaOH (50 ml) and ethyl acetate (250 ml). The organic layer was collected, dried over MgSO4 and evaporated in vacuo. The resulting oil was dissolved in triethylamine (10 ml) and degassed with nitrogen. Pent-4-yn-1-ol (3 g, 0.035 mol) was added, followed by bis(triphenylphosphine)palladium (II) chloride (200 mg) and copper iodide (100 mg). The reaction was heated to reflux and stirred for 15 min. The reaction was partitioned between ethyl acetate (250 ml) and water (50 ml). The organic layer was collected, dried over MgSO4 and evaporated. The residue was chromatographed on silica eluting with ethyl acetate to afford the title compound as a yellow solid (3.14 g). 1H NMR (250 MHz, CDCl3) 1.8 (1H, br s), 1.87 (2H, q), 2.57 (2H, t), 3.81 (2H, br t), 7.24 (2H, dd), 8.78 (2H, dd).

Workup

  1. customThe organic layer was collected
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. dissolutionThe resulting oil was dissolved in triethylamine (10 ml)
  5. customdegassed with nitrogen
  6. temperatureThe reaction was heated
  7. temperatureto reflux
  8. customThe reaction was partitioned between ethyl acetate (250 ml) and water (50 ml)
  9. customThe organic layer was collected
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customThe residue was chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-b266716548dc4c0484f4d81a6061c9f5
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

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