Reacción #5440

Ecuación de reacción

H2O

Potassium t-butoxide

2-bromo-5-methoxyphenyl-propionate

diethyl oxalate

ether

ether

→

desired product

Rendimiento 90.0%

2-Oxo-3-carboethoxy-4-(2-bromo-5-methoxyphenyl)butanoic acid, ethyl ester

Rendimiento 90.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe aqueous layer was separated
2. 2
   Extracciónextracted with ether
3. 3
   SecadoThe ether layer was dried (MgSO4)
4. 4
   Otrothe solvent was evaporated

Procedimiento

Potassium t-butoxide (6.72 g) was suspended in 30 ml of anhydrous ether and cooled to 0° C. A solution of 14.35 g of ethyl 3-(2-bromo-5-methoxyphenyl-propionate and 10.95 g diethyl oxalate in 10 ml ether was added dropwise over 15 min. After 2 at 25° C., the reaction was poured into 100 ml H2O and the aqueous layer was separated, acidified to pH 1 and extracted with ether. The ether layer was dried (MgSO4) and the solvent was evaporated to yield 17.48 g of the desired product as a colorless oil (90%). NMR (CDCl3) δ1.20 (t, 3H), 1.35 (t, 3H), 3.32 (dd, 2H), 3.76 (s, 3H), 4.18 (q, 2H), 4.32 (q, 2H), 4.53 (t, 1H), 6.67 (dd, 1H), 6.80 (d, 1H), 7.40 (d, 1H).

Fuente