Реакция #214200

Уравнение реакции

3-chloroperbenzoic acid

dimethyl sulphide

1-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]-3-oxo-2-butyl acetate

chloroform

3-chloroperbenzoic acid

→

residue

Выход 63.0%

(1R,cis)-2-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]ethylidene diacetate

Выход 63.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 16 hours
3. 3
   ДругоеThe reaction mixture obtained
4. 4
   workup.WAITwas continued for 16 hours
5. 5
   ДругоеThe reaction mixture obtained
6. 6
   Другоеat 20° C.
7. 7
   workup.STIRRINGstirring
8. 8
   workup.WAITwas continued for 15 minutes
9. 9
   Фильтрацияthe suspended material was filtered off
10. 10
    Промывкаthe filtrate was washed with two 20-ml portions of a saturated aqueous solution of sodium hydrogen carbonate and two 20-ml portions of a 10%w aqueous solution of sodium chloride
11. 11
    СушкаThe washed organic phase was dried over anhydrous magnesium sulphate
12. 12
    Другоеthe solvent was evaporated (2 kPa) from the dried liquid

Методика

The contents of a 50-ml flask charged with 1-[2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropyl]-3-oxo-2-butyl acetate prepared as in Embodiment VI above (11.9 mmol, 100% (1R,cis) both spatial configurations around C--C(O)CH3 present), chloroform (10 ml) and 3-chloroperbenzoic acid (26 mmol) were stirred magnetically for five hours at 20° C. Then, another quantity of 3-chloroperbenzoic acid (6 mmol) was added and stirring was continued for 16 hours. The reaction mixture obtained was continued for 16 hours. The reaction mixture obtained was mixed with dimethyl sulphide (2 ml), keeping the temperature at 20° C., stirring was continued for 15 minutes, dichloromethane (30 ml) was added, the suspended material was filtered off, the filtrate was washed with two 20-ml portions of a saturated aqueous solution of sodium hydrogen carbonate and two 20-ml portions of a 10%w aqueous solution of sodium chloride. The washed organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated (2 kPa) from the dried liquid to leave a residue (2.3 g) containing the desired (100% (1R,cis), yield 63%). The nuclear magnetic resonance spectrum of this product showed the following absorptions (using a solution of this product in deuterochloroform and relative to a tetramethylsilane standard):

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