Reaktion #6552

Reaktionsgleichung

water

2,5-dichlorobenzenesulfonyl chloride

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

triethylamine

→

product

Ausbeute 137.9%

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

Ausbeute 137.9%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers separated
2. 2
   ExtraktionThe upper aqueous layer is extracted with 200 mL of methylene chloride
3. 3
   Waschenthe combined organic layers are washed with 200 mL each of saturated sodium bicarbonate solution
4. 4
   Sonstigeremoval of 2,5-dichlorobenzenesulfonyl chloride
5. 5
   SonstigeDrying the solution
6. 6
   Einengenwith magnesium sulfate and concentration in vacuo

Vorschrift

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.

Quelle