Réaction #341837

Équation de réaction

p-toluenesulfonyl chloride

3-butyn-1-ol

pyridine

→

title compound

Rendement 16.0%

but-3-ynyl 4-methylbenzenesulfonate

Rendement 16.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autrequenched with aqueous 1% HCl (5 mL)
2. 2
   AutreThe layers were separated
3. 3
   Lavagethe organic layer was washed with aqueous 1% HCl (5 mL) and brine (5 mL)
4. 4
   SéchageThe organic layer was dried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Autrepurified via column chromatography (4:1 hexanes:EtOAc)

Mode opératoire

To a mixture of 3-butyn-1-ol (0.5 g, 8.3 mmol) in CH2Cl2 (20 mL) and pyridine (1.7 mL, 33.2 mmol) was added p-toluenesulfonyl chloride (1.7 g, 8.7 mmol). This mixture was stirred at ambient temperature for 16 h then diluted with CH2Cl2 (20 mL) and quenched with aqueous 1% HCl (5 mL). The layers were separated and the organic layer was washed with aqueous 1% HCl (5 mL) and brine (5 mL). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (4:1 hexanes:EtOAc) to provide the title compound (0.30 g, 1.3 mmol, 16% yield). MS (DCI/NH3) m/z 242 (M+NH4)+.

Source