Reacción #6551

Ecuación de reacción

water

4-chlorobenzenesulfonyl chloride

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

triethylamine

→

product

Rendimiento 130.1%

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

Rendimiento 130.1%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution slowly warmed to 20°-25° C. over a period of 2 hours
2. 2
   Otrothe layers separated
3. 3
   ExtracciónThe upper aqueous layer is extracted with 200 mL of methylene chloride
4. 4
   Lavadothe combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
5. 5
   Otroremoval of 4-chlorobenzenesulfonyl chloride
6. 6
   OtroDrying the solution
7. 7
   Concentraciónwith magnesium sulfate and concentration in vacuo

Procedimiento

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.

Fuente