Reaktion #5795

Reaktionsgleichung

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

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine until the aqueous washes
2. 2
   TrocknenThe diethyl ether layer is dried (magnesium sulfate)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated

Vorschrift

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.

Quelle