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

HRID 1198353Notes

Reaction equation

HRID 1198353 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-28a97f7064764773a19cfffe27b6548c
Source dataset
uspto-grants-1994_01
Patent number
US05280126

Reaction notes

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