Ozone → (+/-)-cis-6-(2-Oxoethyl)-1,3-dioxane-4-acetonitrile

HRID 1587167Notes

Reaction equation

HRID 1587167 reaction equation
[CH2:1]([C@H:4]1[O:9][CH2:8][O:7][C@@H:6]([CH2:10][C:11]#[N:12])[CH2:5]1)[CH:2]=C.[O:13]=[O+][O-]>ClCCl>[O:13]=[CH:2][CH2:1][C@H:4]1[O:9][CH2:8][O:7][C@@H:6]([CH2:10][C:11]#[N:12])[CH2:5]1

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 67833318(+/-)-cis-6-(2-Propenyl)-1,3-dioxane-4-acetonitrile

Product 1

HCID 86744693(+/-)-cis-6-(2-Oxoethyl)-1,3-dioxane-4-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (±)-cis-6-(2-propenyl)-1,3-dioxane4-acetonitrile, 2.57 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsbach generator, flow rate 0.1, voltage=90 V) is then passed through a fritted gas inlet tube into the solution until the blue color of ozone appears. The current is turned off, and oxygen bubbled through until the blue color is discharged. Triphenylphosphine, 4.87 g (28.58 mmol), is added and the colorless solution is allowed to warm to room temperature. Flash chromatography provides after concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile.

Workup

  1. customoxygen bubbled through until the blue color
  2. additionTriphenylphosphine, 4.87 g (28.58 mmol), is added
  3. customFlash chromatography provides
  4. concentrationafter concentration in vacuo 2.3 g of pure (±)-cis-6-(2-oxoethyl)-1,3-dioxane-4-acetonitrile

Sources & evidence

ORD record
ord-c9cfedbcc5bd4be9a542b50e56aacbd0
Source dataset
uspto-grants-1993_06
Patent number
US05216174

Reaction notes

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