Diethyl Ether → (+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acid

HRID 5699

Reaktionsgleichung

Reaktionsgleichung von HRID 5699
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[O:14]=[CH:15][CH2:16][C@H:17]1[O:22][C:21]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[O:20][C@@H:19]([CH2:28][C:29]#[N:30])[CH2:18]1.C(OCC)C>CC(C)=O>[C:29]([CH2:28][C@H:19]1[O:20][C:21]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[O:22][C@@H:17]([CH2:16][C:15]([OH:3])=[O:14])[CH2:18]1)#[N:30]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 86744692(+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrileHCID 131709961Jones' reagent

Produkt 1

HCID 15045140(+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Jones reagent (chromium trioxide-sulfuric acid-water), 4.4 mL (8.85 mmol), is added dropwise to a 0° C. solution of (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile, 3.62 g (12.6 mmol), dissolved in 30 mL of acetone until the orange color is not discharged. After stirring a further 15 minutes, the mixture is poured into 300 mL of diethyl ether and washed with brine until the aqueous washes are colorless. The diethyl ether layer is dried (magnesium sulfate), filtered, and concentrated to provide 3.65 g of (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid as a yellow solid.

Aufarbeitung

  1. washwashed with brine until the aqueous washes
  2. dry with materialThe diethyl ether layer is dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3d84a1c79e4c48b59df80afeab5d15aa
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245047

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