Reacción #1435730

Ecuación de reacción

hydrochloric acid

sodium hydride

ethyl 2-chloro-6-fluorophenylacetate

acetic anhydride

→

ethyl (2-chloro-6-fluorophenyl)acetoacetate

Rendimiento 35.8%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   Temperaturaunder reflux
3. 3
   Temperaturarefluxed
4. 4
   Temperaturaunder heating for 10 hours
5. 5
   TemperaturaThe reaction mixture was cooled
6. 6
   Extracciónextracted with t-butyl methyl ether
7. 7
   LavadoThe organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water
8. 8
   Secadosubsequently, dried over sodium sulfate
9. 9
   Concentraciónconcentrated

Procedimiento

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.

Fuente