Reacción #5795

Ecuación de reacción

Jones reagent

(±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

diethyl ether

→

(±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine until the aqueous washes
2. 2
   SecadoThe diethyl ether layer is dried (magnesium sulfate)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated

Procedimiento

Jones reagent (chromium trioxide-sulfuric acid-water), 4.4 mL (8.85 mmol), is added dropwise to a 0° C. solution of (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile, 3.62 g (12.6 mmol), dissolved in 30 mL of acetone until the orange color is not discharged. After stirring a further 15 minutes, the mixture is poured into 300 mL of diethyl ether and washed with brine until the aqueous washes are colorless. The diethyl ether layer is dried (magnesium sulfate), filtered, and concentrated to provide 3.65 g of (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid as a yellow solid.

Fuente