Hydrochloric Acid → 2-Phenyl-2-cyclohexen-1-one

HRID 2211148

Reaktionsgleichung

Reaktionsgleichung von HRID 2211148
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([Li])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OC(=O)C)(=[O:18])C.P(Cl)(Cl)(Cl)=O.Cl>N1C=CC=CC=1>[C:1]1([C:10]2[C:9](=[O:18])[CH2:14][CH2:13][CH2:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 178418255HCID 178418255, VerbindungHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 12014012-Phenyl-2-cyclohexen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

When phenylmagnesium bromide (a) or phenyllithium (b) is used in place of 3-pyridylmagnesium bromide, the phenylcarbinol enol ether 13 arises (Scheme 3). This is refluxed with acetic anhydride (c) or dehydrated with phosphorous oxychloride and pyridine (d) and hydrolyzed with aqueous hydrochloric acid (e) to give 2-phenyl-2-cyclohexenone (14). Reduction of 14 with sodium borohydride and cerium chloride in methanol (f) provides the allylic alcohol 15 which is dehydrated (d) to 2-phenyl-1,3-cyclohexadiene 16. Reaction of 16 with tertiary butyl nitrosoformate (2) as in Scheme 1, provides the Diels-Alder cycloadduct 17, which can be converted in four steps to (±) exo-2-phenyl-7-azabicyclo[2.2.1]heptane (18), the phenyl analog of epibatidine. ##STR6##

Quellen und Nachweise

ORD-Eintrag
ord-1e8e2b522c884cc7b6f929328c7f7da2
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05462956

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