Reaktion #69512

Reaktionsgleichung

p-toluenesulfonyl chloride

dichloromethane

2-methoxypropan-1-ol

pyridine

→

title compound

Ausbeute 71.9%

2-Methoxypropyl 4-methylbenzenesulfonate

Ausbeute 71.9%

Lösungsmittel

ethyl acetate

water

n-heptane ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for five hours
2. 2
   workup.STIRRINGAfter thoroughly shaking the mixture
3. 3
   Sonstigethe organic layer was separated
4. 4
   Waschenthe organic layer was washed with brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   FiltrationThe mixture was filtered
7. 7
   workup.DISTILLATIONthe solvent in the filtrate was then distilled off under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Vorschrift

To dichloromethane (30 mL) mixture of 2-methoxypropan-1-ol (1.6 g, 17.8 mmol) and pyridine (20.0 mL), was added p-toluenesulfonyl chloride (4.07 g, 21.4 mmol) while stirring on ice, and the mixture was stirred at room temperature for five hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1) to obtain the title compound (3.12 g, 12.8 mmol).

Quelle