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

HRID 1034186Notes

Reaction equation

HRID 1034186 reaction equation
[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

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 178418255HCID 178418255, compoundHCID 178506676HCID 178506676, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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##

Sources & evidence

ORD record
ord-9f45c10a68514aeab74e6f138068b1ce
Source dataset
uspto-grants-1994_05
Patent number
US05314899

Reaction notes

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