反応 #40577

反応方程式

diisopropylamine

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

methyl iodide

→

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

溶媒

ammonium chloride

THF

n-butyl lithium

THF

反応条件

後処理

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

実験手順

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.

出典