반응 #5783

반응 방정식

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

Ozone

ozone

→

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

용매

dichloromethane

반응 조건

후처리

1. 1
   기타oxygen bubbled through until the blue color
2. 2
   workup.ADDITIONTriphenylphosphine, 4.2 g (16 mmol), is added
3. 3
   기타Flash chromatography provides
4. 4
   농축after concentration in vacuo, 2.5 g of pure (±)-cis-6-(2-oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile

실험 절차

A solution of (±)-cis-2,2-dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 3 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsbach generator, flow rate 0.1, voltage=90 V) 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, 4.2 g (16 mmol), is added and the colorless solution allowed to warm to room temperature. Flash chromatography provides, after concentration in vacuo, 2.5 g of pure (±)-cis-6-(2-oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile.

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