Cornforth reagent → 2-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

反応式

[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=1)[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:2]([C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][C:7]([CH3:15])([CH3:14])[C:6]=2[CH:5]=1)(=[O:1])[CH3:3]

参加物

実験手順

To a stirred solution of 2.44 g (11.96 mmol) of 2-(1-hydroxyethyl)-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene in 35 ml of methylene chloride was added 6.75 g (17.9 mmol) of pyridinium dichromate and 330 mg (1.68 mmol) of pyridinium trifluoroacetate. The mixture was stirred at room temperature for 24 h and then diluted with 35 ml of low-boiling petroleum ether. The mixture was filtered through a short column of anhydrous MgSO4 and silica and the filtrate then concentrated in-vacuo to give the title compound as a colorless oil.