Potassium Cyanide → (+/-)-cis-2,2-Dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

HRID 5686

반응식

HRID 5686 반응식
[C-:1]#[N:2].[K+].[CH2:4]([C@@H:7]([OH:12])[CH2:8][C@@H:9]1[CH2:11][O:10]1)[CH:5]=[CH2:6].[CH:13](O)([CH3:15])[CH3:14].O>>[CH3:14][C:13]1([CH3:15])[O:10][C@@H:9]([CH2:11][C:1]#[N:2])[CH2:8][C@@H:7]([CH2:4][CH:5]=[CH2:6])[O:12]1

참가 물질

4

반응물 3

HCID 9032Potassium CyanideHCID 13895984(R*,R*)-alpha-2-propenyloxiraneethanolHCID 21889133Propan-2-ol--water (1/1)

생성물 1

HCID 15045109(+/-)-cis-2,2-Dimethyl-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 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.

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 2,2-dimethoxypropane
  7. additioncamphorsulfonic acid is added
  8. stirringthe solution stirred for 18 hours at room temperature
  9. concentrationConcentration and flash chromatography

출처 및 근거

ORD 기록
ord-a3a4fee475da4c86890db66cdc3aa76f
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245047

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