反应详情

Potassium cyanide, 1.3 g (20 mmol), is added to a room temperature solution of (R*,R*)-α-2-propenyloxiraneethanol, 2.56 g (20 mmol), in 25 mL of 4:1 isopropanol-water. The solution is stirred for 20 hours at ambient temperature, concentrated, and partitioned between ethyl acetate and brine. The aqueous layer is extracted 2× with ethyl acetate and the combined ethyl acetate extracts are washed with brine and dried (magnesium sulfate). The crude product is dissolved in 20 mL of 2,2-dimethoxypropane, camphorsulfonic acid is added and the solution stirred for 18 hours at room temperature. Concentration and flash chromatography provides 1.30 g of (±)-cis-2,2-dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile.

1. concentrationconcentrated
2. custompartitioned between ethyl acetate and brine
3. extractionThe aqueous layer is extracted 2× with ethyl acetate
4. washthe combined ethyl acetate extracts are washed with brine
5. dry with materialdried (magnesium sulfate)
6. dissolutionThe crude product is dissolved in 20 mL of 2,2-dimethoxypropane
7. additioncamphorsulfonic acid is added
8. stirringthe solution stirred for 18 hours at room temperature
9. concentrationConcentration and flash chromatography