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

HRID 5687

Reaction equation

HRID 5687 reaction equation
[CH3:1][C:2]1([CH3:14])[O:7][C@@H:6]([CH2:8][C:9]#[N:10])[CH2:5][C@@H:4]([CH2:11][CH:12]=C)[O:3]1.[O:15]=[O+][O-]>ClCCl>[O:15]=[CH:12][CH2:11][C@H:4]1[O:3][C:2]([CH3:14])([CH3:1])[O:7][C@@H:6]([CH2:8][C:9]#[N:10])[CH2:5]1

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 15045109(+/-)-cis-2,2-Dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

Product 1

HCID 86744690(+/-)-cis-6-(2-Oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (±)-cis-2,2-dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile, 3 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, 4.2 g (16 mmol), is added and the colorless solution allowed to warm to room temperature. Flash chromatography provides, after concentration in vacuo, 2.5 g of pure (±)-cis-6-(2-oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile.

Workup

  1. customoxygen bubbled through until the blue color
  2. additionTriphenylphosphine, 4.2 g (16 mmol), is added
  3. customFlash chromatography provides
  4. concentrationafter concentration in vacuo, 2.5 g of pure (±)-cis-6-(2-oxoethyl)-2,2-dimethyl-1,3-dioxane-4-acetonitrile

Sources & evidence

ORD record
ord-b6eb58361dae4facaccd1c29d8d6a8b6
Source dataset
uspto-grants-1993_09
Patent number
US05245047

Linked notes

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