反应 #944012

反应方程式

m-chloroperbenzoic acid

Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

sodium thiosulfate

→

title compound

收率 74.0%

Methyl 2-(4-methylthiophenacyl)acetoacetate

收率 74.0%

溶剂

methylene chloride

反应条件

后处理

1. 1
   温度cooling
2. 2
   workup.STIRRINGthe mixture was vigorously shaken
3. 3
   其他after which it separated into liquid phases
4. 4
   其他The organic layer was separated
5. 5
   洗涤washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
6. 6
   干燥after which it was dried over anhydrous magnesium sulfate
7. 7
   其他the solvent was then removed by distillation under reduced pressure
8. 8
   洗涤eluted with a 1:1 by volume mixture of ethyl acetate and hexane

实验过程

43(ii) Methyl 2-(4-methylsulfonylphenacyl)acetoacetate 4.42 g (15.8 mmol) of methyl 2-(4-methylthiophenacyl) acetoacetate [prepared as described in step (i) above] were dissolved in 150 ml of methylene chloride, and 7.77 g (31.5 mmol) of 70% m-chloroperbenzoic acid were added to the resulting solution, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour. 30 ml of a 10% w/v aqueous solution of sodium thiosulfate were added to the mixture, and the mixture was vigorously shaken, after which it separated into liquid phases. The organic layer was separated and washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate and the solvent was then removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1:1 by volume mixture of ethyl acetate and hexane, to give 3.65 g (yield 74%) of the title compound as a slightly yellow powder.

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