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

HRID 893499Notes

Reaction equation

HRID 893499 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-propenyl-oxiraneethanol, 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 2x 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 2x 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-1488fc5da96a498e924a0f6cedf4fcb7
Source dataset
uspto-grants-1992_06
Patent number
US05124482

Reaction notes

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