Dimethyl Sulfide → 2-Carbomethoxymethyl-5-ethenyl-2-ethylcyclohexanone

HRID 483131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483131
[C:1]([CH2:5][C:6]1([CH2:13][CH3:14])[C:11](=[O:12])[CH:10]=[CH:9][CH2:8][CH2:7]1)([O:3][CH3:4])=[O:2].S(C)C.[CH:18]([Mg]Br)=[CH2:19]>C1COCC1>[C:1]([CH2:5][C:6]1([CH2:13][CH3:14])[CH2:7][CH2:8][CH:9]([CH:18]=[CH2:19])[CH2:10][C:11]1=[O:12])([O:3][CH3:4])=[O:2]

Komponenten

5

Edukt 3

HCID 1068Dimethyl Sulfide2×HCID 136492416-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-oneHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 142014342-Carbomethoxymethyl-5-ethenyl-2-ethylcyclohexanoneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The enone, 6-carbomethoxymethyl-6-ethyl-2-cyclohexen-1-one, prepared by the process of Step (c) (58.1 mmol, 11.4 g), 5.81 mmol (1.194 g) of CuBr.Me2S and 11.7 ml of Me2S were stirred in 176 ml of THF at -40° C. under nitrogen and treated with 58.1 mmol (58.1 ml of 1M solution in THF) of vinylmagnesium bromide added dropwise over 45 minutes. The reaction was then quenched with 200 ml of 1M HCl (aq.) and extracted with 5×100 ml of petroleum ether. Drying (MgSO4) and flash chromatography afforded 8.96 g (39.9 mmol, 69% pale yellow oil) of product as a mixture of diastereomers. The diastereomers (56:44 ratio) were separated by preparative HPLC on a Prep 500A using a brand of silica gel available from Waters Associates, Milford, Ma., and designated "more polar isomer" and "less polar isomer."

Aufarbeitung

  1. additionadded dropwise over 45 minutes
  2. customThe reaction was then quenched with 200 ml of 1M HCl (aq.)
  3. extractionextracted with 5×100 ml of petroleum ether
  4. dry with materialDrying (MgSO4) and flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79d499814b2341afa98bdcffec7ad545
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578398

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