Diethyl Ether → 2,2-Dichloro-3-oxocyclobutyl pivalate

HRID 1039687

Reaktionsgleichung

Reaktionsgleichung von HRID 1039687
[C:1](OC=C)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl[C:11]([Cl:16])([Cl:15])[C:12](Cl)=[O:13].[O-][Mn](=O)(=O)=O.[K+].[CH3:23][CH2:24][O:25]CC>[Zn]>[C:1]([O:13][CH:12]1[CH2:23][C:24](=[O:25])[C:11]1([Cl:16])[Cl:15])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 3283Diethyl Ether2×HCID 6420Trichloroacetyl chlorideHCID 256591Vinyl pivalateHCID 516875Potassium Permanganate

Produkt 1

HCID 575158702,2-Dichloro-3-oxocyclobutyl pivalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a stirred mixture of vinyl pivalate (30 g, 234 mmol) and zinc (31 g, 468 mmol) in ether (300 ml) was added a solution of 2,2,2-trichloroacetyl chloride (55 g, 304 mmol) in ether (300 ml) dropwise (2-3 h) in a water bath. (Note: fast addition causes the reaction temp. to elevate) while maintaining the reaction temperature between 15-30° C. After the reaction was done (stained with KMnO4 solution), it was filtered through Celite. The filtrate was washed with cold water, brine, dried over MgSO4 and concentrated to give the title compound as an orange solid.

Aufarbeitung

  1. addition(Note: fast addition
  2. customthe reaction temp
  3. filtrationwas filtered through Celite
  4. washThe filtrate was washed with cold water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6b2f71b9ca664154ab9f6b8a0f955db1
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552181B2

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