Reacción #1110280

Ecuación de reacción

LiHMDS

46b

1-(4-Chloro-phenyl)-2-methyl-pent-1-en-3-one

diethyl oxalate

→

46c

Rendimiento 97.6%

Ethyl 6-(4-chloro-phenyl)-3,5-dimethyl-2,4-dioxo-hex-5-enoate

Rendimiento 97.6%

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring at −78° C. for 1 h
2. 2
   Temperaturathe mixture was warmed up to room temperature
3. 3
   workup.STIRRINGstirred overnight
4. 4
   OtroThe solvent was evaporated
5. 5
   Lavadowashed with 1N HCl and brine
6. 6
   SecadoThe organic layer was dried over Na2SO4
7. 7
   Concentraciónconcentrated

Procedimiento

To a solution of LiHMDS (1N solution in THF, 5.48 mmol, 5.17 mL) in THF (16 mL) at −78° C. was added a solution of 46b (4.98 mmol, 1.04 g) in THF (2.5 mL) drop wise. After stirring at −78° C. for 1 h, the mixture was treated with a solution of diethyl oxalate (4.98 mmol, 0.73 g) in THF (2.5 mL). After stirring at −78° C. for 1 h, then the mixture was warmed up to room temperature and stirred overnight. The solvent was evaporated and the crude product was taken up in EtOAc, and washed with 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated to give 1.5 g of 46c.

Fuente