반응 #6552

반응 방정식

water

2,5-dichlorobenzenesulfonyl chloride

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

triethylamine

→

product

수율 137.9%

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

수율 137.9%

용매

methylene chloride

반응 조건

후처리

1. 1
   기타the layers separated
2. 2
   추출The upper aqueous layer is extracted with 200 mL of methylene chloride
3. 3
   세척the combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
4. 4
   기타removal of 2,5-dichlorobenzenesulfonyl chloride
5. 5
   기타Drying the solution
6. 6
   농축with magnesium sulfate and concentration in vacuo

실험 절차

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.

출처