Реакция #1435730

Уравнение реакции

hydrochloric acid

sodium hydride

ethyl 2-chloro-6-fluorophenylacetate

acetic anhydride

→

ethyl (2-chloro-6-fluorophenyl)acetoacetate

Выход 35.8%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   Температураunder reflux
3. 3
   Температураrefluxed
4. 4
   Температураunder heating for 10 hours
5. 5
   ТемператураThe reaction mixture was cooled
6. 6
   Экстракцияextracted with t-butyl methyl ether
7. 7
   ПромывкаThe organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water
8. 8
   Сушкаsubsequently, dried over sodium sulfate
9. 9
   Концентрированиеconcentrated

Методика

Into a mixture of 9.6 g of sodium hydride (60% in oil) and 200 ml of tetrahydrofuran, 21.7 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under reflux. Then, a solution of 12.3 g of acetic anhydride in 40 ml tetrahydrofuran was added thereto and refluxed under heating for 10 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water, subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 9.27 g of ethyl (2-chloro-6-fluorophenyl)acetoacetate.

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