반응 #5798

반응 방정식

isopropanol

Potassium cyanide

(R*,R*)-α-2-propenyloxiraneethanol

water

→

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

반응 조건

후처리

1. 1
   농축concentrated
2. 2
   기타partitioned between ethyl acetate and brine
3. 3
   추출The aqueous layer is extracted 2× with ethyl acetate
4. 4
   세척the combined ethyl acetate extracts are washed with brine
5. 5
   건조dried (magnesium sulfate)
6. 6
   workup.DISSOLUTIONThe crude product is dissolved in 20 mL of dimethoxymethane
7. 7
   workup.ADDITIONcamphorsulfonic acid is added
8. 8
   workup.STIRRINGthe solution is stirred for 18 hours at room temperature
9. 9
   농축Concentration and flash chromatography
10. 10
    농축after concentration in vacuo

실험 절차

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 dimethoxymethane, camphorsulfonic acid is added, and the solution is stirred for 18 hours at room temperature. Concentration and flash chromatography after concentration in vacuo provides 1.20 g of (±)-cis-6-(2-propenyl)-1,3-dioxane-4-acetonitrile.

출처