Water → (+/-)-cis-6-(2-Propenyl)-1,3-dioxane-4-acetonitrile

HRID 5702

반응식

HRID 5702 반응식
[C-:1]#[N:2].[K+].[CH2:4]([C@@H:7](O)[CH2:8][C@@H:9]1[CH2:11][O:10]1)C=C.O.[CH:14]([OH:17])([CH3:16])[CH3:15]>>[CH2:8]([C@H:9]1[O:10][CH2:11][O:17][C@@H:14]([CH2:16][C:1]#[N:2])[CH2:15]1)[CH:7]=[CH2:4]

참가 물질

5

반응물 4

HCID 962WaterHCID 3776IsopropanolHCID 9032Potassium CyanideHCID 13895984(R*,R*)-alpha-2-propenyloxiraneethanol

생성물 1

HCID 67833318(+/-)-cis-6-(2-Propenyl)-1,3-dioxane-4-acetonitrile

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.

후처리

  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 dimethoxymethane
  7. additioncamphorsulfonic acid is added
  8. stirringthe solution is stirred for 18 hours at room temperature
  9. concentrationConcentration and flash chromatography
  10. concentrationafter concentration in vacuo

출처 및 근거

ORD 기록
ord-148fb88f54bc47f586ea0de1d06b0d0a
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245047

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