Hydrochloric Acid → 6-(3-Chloro-2-oxopropyl)-2,2-dimethyl-2H,4H-1,3-dioxin-4-one

HRID 1657198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657198
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3]1.[Cl:11][CH2:12][C:13](Cl)=[O:14].[Li+].CC([N-]C(C)C)C.Cl>C(OCC)(=O)C.CCOCC>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][C:13](=[O:14])[CH2:12][Cl:11])[O:3]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 149448286-(3-Chloro-2-oxopropyl)-2,2-dimethyl-2H,4H-1,3-dioxin-4-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In an argon gas stream, 20.6 ml of n-butyl lithium (1.6M solution in hexane) were added to 60 ml of an ether solution containing 3.53 g (0.033 mol) of diisopropylamine at -20° C. to form LDA. After stirring for 30 minutes, a mixture of 4.26 g (0.03 mol) of 2,2-dimethyl-6-methyl-1,3-dioxin-4-one and 60 ml of ether as well as 60 ml of an ether solution containing 1.69 g (0.015 mol) of chloroacetyl chloride were added to LDA. After the temperature was gradually returned to room temperature, 10% hydrochloric acid was added thereto to neutralize the solution, and extraction was then carried out with ether. The resultant organic layer was dried over anhydrous magnesium sulfate. Next, the solvent was distilled off, and the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate =4:1), thereby obtaining 2.26 g (yield 69%) of 2,2-dimethyl-6-(3-chloro-2-oxopropyl)-1, 3-dioxin-4 -one.

Aufarbeitung

  1. customwas gradually returned to room temperature
  2. extractionthe solution, and extraction
  3. dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
  4. distillationNext, the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-869ba30ddd7c442d86a0c3d74ba9675d
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256800

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