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

HRID 5703

Reaction equation

HRID 5703 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-dioxane-4-acetonitrile, 2.57 g (15.36 mmol), in 100 mL of dichloromethane is cooled to -78° C. under nitrogen. Ozone (Welsback generator, flow rate 0.1, voltage=90V) 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-fd5a9b495e42491992d07ec5b729edec
Source dataset
uspto-grants-1993_09
Patent number
US05245047

Linked notes

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