Реакция #40577

Уравнение реакции

diisopropylamine

methyl 2-(4-chlorophenyl)-2-cyclopentylacetate

methyl iodide

→

methyl 2-(4-chlorophenyl)-2-cyclopentylpropionate

Растворители

ammonium chloride

THF

n-butyl lithium

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter 15 minutes' stirring
2. 2
   ДругоеThe reaction liquid temperature
3. 3
   Температураwas raised to 0° C.
4. 4
   workup.STIRRINGthe liquid was stirred for 1.5 hours
5. 5
   Экстракцияextracted with diethyl ether
6. 6
   ПромывкаThe organic layer was washed with saturated brine
7. 7
   Сушкаdried over anhydrous sodium sulfate and condensed under reduced pressure
8. 8
   ДругоеThe resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate 60/1)

Методика

To a solution of diisopropylamine (0.15 ml) in THF (2 ml), n-butyl lithium (1.5 M hexane solution, 0.6 ml) was added at −78° C., stirred for 10 minutes and another solution of methyl 2-(4-chlorophenyl)-2-cyclopentylacetate (200 mg) in THF (1.5 ml) was added dropwise. After 15 minutes' stirring, the system temperature was raised to −35° C., and methyl iodide (0.15 ml) was added. The reaction liquid temperature was raised to 0° C., and the liquid was stirred for 1.5 hours, diluted with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and condensed under reduced pressure. The resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate 60/1) to provide methyl 2-(4-chlorophenyl)-2-cyclopentylpropionate (180 mg) as yellow oily substance.

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