تفاعل #493549

معادلة التفاعل

sodium bicarbonate

Methyl dichlorophosphate

5-chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanoic acid amide

1,8-diazabicyclo[5,4,0]undec-7-ene

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title compound

المردود 79.6%

5-chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanenitrile

المردود 79.6%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter completion of the dropwise addition
2. 2
   workup.STIRRINGAfter stirring for five minutes
3. 3
   أخرىthe organic layer was separated
4. 4
   غسيلThe combined organic layers were sequentially washed with 1 N hydrochloric acid, water
5. 5
   تجفيفa saturated sodium bicarbonate aqueous solution and brine, dried over anhydrous magnesium sulfate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe resulting residue was purified by silica gel column chromatography (carrier: Wakogel C-200; elution solvent:heptane:ethyl acetate=49:1→19:1)

الإجراء التجريبي

Methyl dichlorophosphate (1.9 mL) was added dropwise at 20° C. or less to an ice-cooled solution of 5-chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanoic acid amide (3.0 g) and 1,8-diazabicyclo[5,4,0]undec-7-ene (6.4 mL) in methylene chloride (30 mL). After completion of the dropwise addition, the reaction solution was stirred at room temperature for one hour and 25 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction solution. After stirring for five minutes, the organic layer was separated. The aqueous layer was reextracted with methylene chloride. The combined organic layers were sequentially washed with 1 N hydrochloric acid, water, a saturated sodium bicarbonate aqueous solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Wakogel C-200; elution solvent:heptane:ethyl acetate=49:1→19:1) to obtain 2.25 g of the title compound.

المصدر