Dimethyl Sulfoxide → 4-(Propynyloxy)pyridine

HRID 27041

Reaction equation

HRID 27041 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.CS(C)=O.[CH2:12](Cl)[C:13]#[CH:14]>O.C(=O)([O-])[O-].[Ag+2]>[C:12]([O:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)#[C:13][CH3:14]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 122213-Chloro-1-propyneHCID 178418642HCID 178418642, compound

Product 1

HCID 233434924-(Propynyloxy)pyridineYield 3.6%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of 20.0 g (0.21 mole) 4-hydroxypyridine and 200 ml dimethyl sulfoxide was added 102 g (0.1 mole) silver carbonate. Propargyl chloride (22.5 g, 0.3 mole) was added to this suspension and the mixture heated at 50° for 6 hrs. After cooling to room temperature, the reaction mixture was diluted with water and extracted two times with ether. The combined ether extract was dried, filtered and concentrated as before to give 1.0 g of 4-(propynyloxy)pyridine. The product was 95% pure by vpc. The nmr and ir were compatible with the structure.

Workup

  1. temperaturethe mixture heated at 50° for 6 hrs
  2. extractionextracted two times with ether
  3. extractionThe combined ether extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated as before

Sources & evidence

ORD record
ord-6a8c1777713940babd8f296f2d89bc27
Source dataset
uspto-grants-1980_09
Patent number
US04220577

Linked notes

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