반응 #6551

반응 방정식

water

4-chlorobenzenesulfonyl chloride

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

triethylamine

→

product

수율 130.1%

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

수율 130.1%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도the solution slowly warmed to 20°-25° C. over a period of 2 hours
2. 2
   기타the layers separated
3. 3
   추출The upper aqueous layer is extracted with 200 mL of methylene chloride
4. 4
   세척the combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
5. 5
   기타removal of 4-chlorobenzenesulfonyl chloride
6. 6
   기타Drying the solution
7. 7
   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 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.

출처