3-Bromofuran → (1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

反応式

[Br:1][C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[I-].[Mg+2].[I-].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[CH:19]1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1=[O:25]>ClCCl>[Br:1][C:2]1[CH:3]2[O:4][CH:5]([CH:6]=1)[CH:21]1[CH:22]2[C:23](=[O:24])[CH:19]([C:12]2[C:11]([CH3:10])=[CH:16][C:15]([CH3:17])=[CH:14][C:13]=2[CH3:18])[C:20]1=[O:25]

参加物

実験手順

3-Bromofuran (5.2 g, 56 mmol) and magnesium iodide (1.5 g, 5.6 mmol) are added to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (4.0 g, 18.7 mmol) and the mixture is stirred at room temperature for 2 days; small quantities of dichloromethane are added when required to aid stirring. The reaction mixture is allowed to stand at room temperature for 17 hours, then concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione.