Reaktion #69509

Reaktionsgleichung

water

3-hydroxytetrahydrofuran

pyridine

p-toluenesulfonyl chloride

→

title compound

Ausbeute 67.5%

Tetrahydrofuran-3-yl-4-methylbenzenesulfonate

Ausbeute 67.5%

Lösungsmittel

n-heptane ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred for 8.5 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 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 a mixture of 3-hydroxytetrahydrofuran (7.00 g, 79.5 mmol) and pyridine (100 mL), was added p-toluenesulfonyl chloride (18.2 g, 95.4 mmol) while stirring at room temperature, and the resulting mixture was stirred for 8.5 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 then the solvent in the filtrate was 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=4/1) to obtain the title compound (13.0 g, 53.7 mmol).

Quelle