Reaktion #68027

Reaktionsgleichung

8-(2-hydroxyethyl)-1,4-dioxaspiro(4.5)decan-8-ol

pyridine

p-toluenesulfonyl chloride

→

2-(8-hydroxy-1,4-dioxaspiro(4.5)decan-8-yl)ethyl 4-methylbenzenesulfonate

Lösungsmittel

chloroform

chloroform

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   Temperaturunder cooling with ice
3. 3
   workup.WAITleft
4. 4
   workup.WAITto stand overnight
5. 5
   workup.STIRRINGfurther stirred at 30 to 40° C. for 1 hour
6. 6
   Temperaturunder cooling with ice
7. 7
   SonstigeThe organic layer was separated
8. 8
   Waschenwashed with an aqueous saturated sodium chloride solution
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Sonstigethe solvent was removed under reduced pressure
11. 11
    SonstigeThe residue thus obtained
12. 12
    Sonstigewas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Vorschrift

To 30 mL of a chloroform solution containing 4.2 g of 8-(2-hydroxyethyl)-1,4-dioxaspiro(4.5)decan-8-ol, 2.18 mL of pyridine was added at room temperature, and 4.0 g of p-toluenesulfonyl chloride was dividedly added thereto under cooling with ice, the mixture was stirred at room temperature for 1 hour and 35 minutes, left to stand overnight, and then further stirred at 30 to 40° C. for 1 hour. The reaction mixture was added with water and chloroform under cooling with ice. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1] to obtain 4.2 g of a yellow oily substance, 2-(8-hydroxy-1,4-dioxaspiro(4.5)decan-8-yl)ethyl 4-methylbenzenesulfonate.

Quelle