反应 #6550

反应方程式

water

4-bromobenzenesulfonyl chloride

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

triethylamine

→

product

收率 144.4%

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

收率 144.4%

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他the layers separated
2. 2
   萃取The upper aqueous layer is extracted with 250 mL of methylene chloride
3. 3
   洗涤the combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
4. 4
   其他removal of 4-bromobenzenesulfonyl chloride
5. 5
   其他Drying the solution
6. 6
   浓缩with magnesium sulfate and concentration in vacuo

实验过程

To a stirring, 20°-25° 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-bromobenzenesulfonyl chloride (15 g, 57.5 mmol). Stirring is continued at 20°-25° C. for 20 hours, the solution is poured onto 250 mL of water and the layers separated. The upper aqueous layer is extracted with 250 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-bromobenzenesulfonyl chloride and then saturates sodium chloride solution. Drying the solution with magnesium sulfate and concentration in vacuo gives 26.3 g of the product as a light orange solid.

来源