Reaktion #6555

Reaktionsgleichung

water

4-chlorobenzenesulfonyl chloride

(4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

triethylamine

→

product

Ausbeute 130.1%

(4R-cis)-1,1-dimethylethyl 6-(4-chlorobenzenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

Ausbeute 130.1%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution slowly warmed to 20°-25° C. over a period of 2 hours
2. 2
   Sonstigethe layers separated
3. 3
   ExtraktionThe upper aqueous layer is extracted with 200 mL of methylene chloride
4. 4
   Waschenthe combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
5. 5
   Sonstigeremoval of 4-chlorobenzenesulfonyl chloride
6. 6
   SonstigeDrying the solution
7. 7
   Einengenwith magnesium sulfate and concentration in vacuo

Vorschrift

To a stirring, 0°-5° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (European Patent Application 0319,847) (10 g, 38 mmol) in methylene chloride (250 mL) containing triethylamine (10 mL, 72 mmol) is added 4-chlorobenzenesulfonyl chloride (12.7 g, 60 mmol). Stirring is continued at 0°-5° C. for 2.5 hours and the solution slowly warmed to 20°-25° C. over a period of 2 hours. The solution is poured onto 200 mL of water and the layers separated. The upper aqueous layer is extracted with 200 mL of methylene chloride and the combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution to ensure complete removal of 4-chlorobenzenesulfonyl chloride and then saturated sodium chloride solution. Drying the solution with magnesium sulfate and concentration in vacuo gives 21.5 g of the product as a pale yellow solid.

Quelle