Ozone → (+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

HRID 5698

Reaktionsgleichung

Reaktionsgleichung von HRID 5698
[CH2:1]([C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]#[N:17])[CH2:5]1)[CH:2]=C.[O:18]=[O+][O-]>ClCCl>[O:18]=[CH:2][CH2:1][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]#[N:17])[CH2:5]1

Komponenten

4

Edukt 2

HCID 24823Ozone2×HCID 15045136(+/-)-cis-4-(2-Propenyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

Produkt 1

HCID 86744692(+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (±)-cis-4-(2-propenyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile 4.26 g (19.42 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, 5.6 g (21.36 mmol), is added and the colorless solution is allowed to warm to room temperature. Flash chromatography provides after concentration in vacuo 4.04 g of pure (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile.

Aufarbeitung

  1. customoxygen bubbled through until the blue color
  2. additionTriphenylphosphine, 5.6 g (21.36 mmol), is added
  3. customFlash chromatography provides
  4. concentrationafter concentration in vacuo 4.04 g of pure (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-3f5b0f028a854ac0a60d81cd2b219033
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245047

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