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

HRID 5695

Reaktionsgleichung

Reaktionsgleichung von HRID 5695
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 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 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d15cd1699d9c4e79a33d560421fd6908
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245047

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