Dimethyl Sulfoxide → 4-(Propynyloxy)pyridine
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
Product 1
Reagents, catalysts & solvents 2
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
- temperaturethe mixture heated at 50° for 6 hrs
- extractionextracted two times with ether
- extractionThe combined ether extract
- customwas dried
- filtrationfiltered
- concentrationconcentrated as before
Sources & evidence
- ORD record
- ord-6a8c1777713940babd8f296f2d89bc27
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220577
Reaction notes
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