Triethylamine → HCID 69179494, compound

HRID 1251127Notes

Reaction equation

HRID 1251127 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH2:10][OH:11])=[N:6][CH:7]=1.C(N([CH2:17][CH3:18])CC)C.[CH3:19]S(Cl)(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH2:10][O:11][CH:17]([CH3:18])[CH3:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53717039HCID 53717039, compound

Product 1

HCID 69179494HCID 69179494, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-(3-hydroxy-1-propenyl)pyridine (8.891 g) was dissolved in tetrahydrofuran (200 ml), followed by the sequential addition of triethylamine (17.6 ml) and methanesulfonyl chloride (3.9 ml) under ice-cooling, and the mixture was stirred for 20 min. After the resulting insoluble matters were filtered off, the solution was evaporated. The resulting residue was dissolved in 2-propanol (100 ml), sodium 2-propanoxide/2-propanol solution prepared from 60% sodium hydride (2 g) and 2-propanol (70 ml) was added thereto under ice-cooling, and the resulting mixture was stirred, as it was, at room temperature for 30 min. After the resulting insoluble matters were filtered off from the reaction mixture, the resulting solution was evaporated and partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a brown oil (3.519 g, yield; 33%).

Workup

  1. temperaturecooling
  2. filtrationAfter the resulting insoluble matters were filtered off
  3. customthe solution was evaporated
  4. dissolutionThe resulting residue was dissolved in 2-propanol (100 ml)
  5. customsodium 2-propanoxide/2-propanol solution prepared from 60% sodium hydride (2 g) and 2-propanol (70 ml)
  6. additionwas added
  7. temperatureunder ice-cooling
  8. stirringthe resulting mixture was stirred, as it
  9. waitwas, at room temperature for 30 min
  10. filtrationAfter the resulting insoluble matters were filtered off from the reaction mixture
  11. customthe resulting solution was evaporated
  12. custompartitioned between ethyl acetate and water
  13. washThe resulting organic layer was washed with water
  14. dry with materialdried (over MgSO4)
  15. customevaporated
  16. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-cb83262358b44232a4867af0b363141e
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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