Réaction #555329

Équation de réaction

LiHMDS

46b

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

diethyl oxalate

→

46c

Rendement 97.6%

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

Rendement 97.6%

Solvants

THF

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGAfter stirring at −78° C. for 1 h
2. 2
   Températurethe mixture was warmed up to room temperature
3. 3
   workup.STIRRINGstirred overnight
4. 4
   AutreThe solvent was evaporated
5. 5
   Lavagewashed with 1N HCl and brine
6. 6
   SéchageThe organic layer was dried over Na2SO4
7. 7
   Concentrationconcentrated

Mode opératoire

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.

Source