تفاعل #6552

معادلة التفاعل

water

2,5-dichlorobenzenesulfonyl chloride

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

triethylamine

→

product

المردود 137.9%

(4R-cis)-1,1-dimethylethyl 6-(2,5-dichlorobenzenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

المردود 137.9%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers separated
2. 2
   استخلاصThe upper aqueous layer is extracted with 200 mL of methylene chloride
3. 3
   غسيلthe combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
4. 4
   أخرىremoval of 2,5-dichlorobenzenesulfonyl chloride
5. 5
   أخرىDrying the solution
6. 6
   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 2,5-dichlorobenzenesulfonyl chloride (14.7 g, 57.5 mmol). Stirring is continued at 0°-5° C. for 3.5 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 2,5-dichlorobenzenesulfonyl chloride and then saturated sodium chloride solution. Drying the solution with magnesium sulfate and concentration in vacuo gives 24.6 g of the product as a yellow-orange oil.

المصدر