Ozone → (+/-)-cis-9-(2-Oxoethyl)-6,10-dioxaspiro[4.5]decane-7-acetonitrile

HRID 360017Notes

Reaction equation

HRID 360017 reaction equation
[CH2:1]([C@H:4]1[O:13][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[O:7][C@@H:6]([CH2:14][C:15]#[N:16])[CH2:5]1)[CH:2]=C.[O:17]=[O+][O-]>ClCCl>[O:17]=[CH:2][CH2:1][C@H:4]1[O:13][C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[O:7][C@@H:6]([CH2:14][C:15]#[N:16])[CH2:5]1

Participants

4

Reactant 2

HCID 24823Ozone2×HCID 67833083(+/-)-cis-9-(2-Propenyl)-6,10-dioxaspiro[4.5]decane-7-acetonitrile

Product 1

HCID 86744691(+/-)-cis-9-(2-Oxoethyl)-6,10-dioxaspiro[4.5]decane-7-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (±)-cis-9-(2-propenyl)-6,10-dioxaspiro[4.5]decane-7-acetonitrile, 3.4 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 when 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 is allowed to warm to room temperature. Flash chromatography provides after concentration in vacuo 2.5 g of pure (±)-cis-9-(2-oxoethyl)-6,10-dioxaspiro[4.5]decane-7-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-9-(2-oxoethyl)-6,10-dioxaspiro[4.5]decane-7-acetonitrile

Sources & evidence

ORD record
ord-3ddc099da84f45bd91c3970ed97d286b
Source dataset
uspto-grants-1991_03
Patent number
US05003080

Reaction notes

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