Methyl 3-bromo-1-adamantaneacetate → Methyl 3-phenyl-1-adamantaneacetate

反応式

[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([OH:20])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]12CC3CC(CC(CC(OC)=O)(C3)C1)C2.[Cl-].[Cl-].[Cl-].[Al+3]>C1C=CC=CC=1>[C:1]1([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([CH2:17][C:18]([O:20][CH3:22])=[O:19])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

実験手順

Preparation of 3-Phenyl-l-adamantaneacetic acid, a hapten. Methyl 3-bromoadamantaneacetate (80 g) (Aldrich Chemical Co. Milwaukee Wis.) was dissolved in benzene (1.6 L) under nitrogen. Aluminum trichloride (37.12 g) was added portionwise over 75 min. at ambient temperature. The reaction mixture was then quenched by the addition of 0.5M phosphoric acid (1.6 L). The layers were separated and the organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to give methyl 3-phenyl-1-adamantaneacetate (80 g).