4-Bromopyridinium chloride → HCID 66799224, compound

HRID 1193385Notes

Reaction equation

HRID 1193385 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CC([O-])(C)C.[K+].Cl.Br[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>CS(C)=O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 881004-Bromopyridinium chlorideHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 66799224HCID 66799224, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-ol (4.93 g, 31.202 mmol, 1.0 eq.) was dissolved in DMSO (100 ml); potassium tert-butylate (10.5 g, 93.61 mmol, 3.0 eq.) was added at 0° C. and the mixture was stirred for 1 hour at RT. 4-Bromopyridine HCl (9.1 g, 46.803 mmol, 1.5 eq.) was then added at 0° C. and stirring was carried out for 16 hours at RT. After monitoring by TLC, the reaction mixture was concentrated and the residue was taken up in water (200 ml) and extracted with DCM (2×200 ml). The combined org. phases were washed with water (200 ml) and sat. NaCl solution (250 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 40% ethyl acetate in hexane). Yield: 35% (2.6 g, 11.063 mmol)

Workup

  1. stirringstirring
  2. waitwas carried out for 16 hours at RT
  3. concentrationthe reaction mixture was concentrated
  4. extractionextracted with DCM (2×200 ml)
  5. washphases were washed with water (200 ml) and sat. NaCl solution (250 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (silica gel, 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a5bf59af0d644fddbf9e9ecc8f1e3019
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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