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

HRID 1034186ノート

反応式

HRID 1034186 の反応式
[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

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 178418255HCID 178418255、化合物HCID 178506676HCID 178506676、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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##

出典と根拠

ORDレコード
ord-9f45c10a68514aeab74e6f138068b1ce
出典データセット
uspto-grants-1994_05
特許番号
US05314899

反応ノート

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