Реакция #2486954

Уравнение реакции

lithium diisopropylamide

diisopropylamine

methyl iodide

n-butyl lithium

ethyl 4-chlorophenylacetate

→

ethyl 2-(4-chlorophenyl)propionate

Растворители

THF

hexane

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ether
2. 2
   ПромывкаThe organic layer was washed with water
3. 3
   Сушкаdried over anhydrous magnesium sulfate
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   workup.DISTILLATIONThe resulting residue was distilled under reduced pressure

Методика

To a solution of lithium diisopropylamide (LDA) in THF (1 liter), which had been prepared from diisopropylamine (52 g) and a 1.6 M solution of n-butyl lithium in hexane (319 ml), was added dropwise a solution of ethyl 4-chlorophenylacetate (97.3 g) in THF (100 ml) at a temperature of -45° to -40° C. under an atmosphere of nitrogen gas. At the same temperature, the reaction mixture was stirred for 0.5 hours, and methyl iodide (73 g) was added dropwise thereto, followed by allowing the temperature to gradually increase to room temperature. The reaction mixture was poured into ice-water and extracted with ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure to give ethyl 2-(4-chlorophenyl)propionate (yield, 89.4 g), b.p., 108°-114° C. at 1.0 mmHg.

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