3-Bromopyridine → HCID 54134237, compound

HRID 1494072Notes

Reaction equation

HRID 1494072 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][O:6][C:5](=[O:9])[CH2:4]1)=[CH2:2].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1>C(N(CC)CC)C.C(#N)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH:2]=[CH:1][CH:3]2[CH2:8][CH2:7][O:6][C:5](=[O:9])[CH2:4]2)[CH:34]=1

Participants

8

Reactant 3

HCID 122863-BromopyridineHCID 80271Tri-o-tolylphosphineHCID 5431332H-Pyran-2-one, 4-ethenyltetrahydro-

Product 1

HCID 54134237HCID 54134237, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 0.879 g (7 mmol) of 4-ethenyltetrahydro-2H-pyran-2-one in 5 mL triethylamine and 5 mL acetonitrile is added 0.081 g (0.36 mmol) Palladium-(II)-acetate followed by 0.659 g (2.5 mmol) tri-o-tolylphosphine and 0.76 mL (7.9 mmol) 3-bromopyridine and the mixture is heated at 125° C. for 20 hours in a sealed tube. It is then cooled, diluted with methylene chloride and washed with water. The organic phase is dried (MgSO4), filtered and evaporated to give a reddish oil which is flash chromatographed using ethyl acetate as eluent to obtain 4-[2-(3-pyridyl)ethenyl]tetrahydro-2H-pyran-2-one as an oil.

Workup

  1. temperatureIt is then cooled
  2. washwashed with water
  3. dry with materialThe organic phase is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a reddish oil which
  7. customchromatographed

Sources & evidence

ORD record
ord-0aa83af016904c829a5c1af2f495544e
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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