反応 #5799

反応方程式

(±)-cis-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

Ozone

ozone

→

(±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他oxygen bubbled through until the blue color
2. 2
   workup.ADDITIONTriphenylphosphine, 4,87 g (28.58 mmol), is added
3. 3
   その他Flash chromatography provides
4. 4
   濃縮after concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile

実験手順

A solution of (±)-cis-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 2.57 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsback generator, flow rate 0.1, voltage=90V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone appears. The current is turned off, and oxygen bubbled through until the blue color is discharged. Triphenylphosphine, 4,87 g (28.58 mmol), is added and the colorless solution is allowed to warm to room temperature. Flash chromatography provides after concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile.

出典