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

HRID 1886267

Reaction equation

HRID 1886267 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 cooed 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. customis cooed to -78° C. under nitrogen
  2. customoxygen bubbled through until the blue color
  3. additionTriphenylphosphine, 4.2 g (16 mmol), is added
  4. customFlash chromatography provides
  5. 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-117d6c3ad65c49bca7ce033c2098fb15
Source dataset
uspto-grants-1992_09
Patent number
US05149837

Linked notes

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