تفاعل #5795

معادلة التفاعل

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

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with brine until the aqueous washes
2. 2
   تجفيفThe diethyl ether layer is dried (magnesium sulfate)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر