تفاعل #6555

معادلة التفاعل

water

4-chlorobenzenesulfonyl chloride

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

triethylamine

→

product

المردود 130.1%

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

المردود 130.1%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution slowly warmed to 20°-25° C. over a period of 2 hours
2. 2
   أخرىthe layers separated
3. 3
   استخلاصThe upper aqueous layer is extracted with 200 mL of methylene chloride
4. 4
   غسيلthe combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
5. 5
   أخرىremoval of 4-chlorobenzenesulfonyl chloride
6. 6
   أخرىDrying the solution
7. 7
   تركيزwith magnesium sulfate and concentration in vacuo

الإجراء التجريبي

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.

المصدر