Furan → 4-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-10-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

반응식

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[C:10]([CH:15]3[C:19](=[O:20])[CH:18]=[CH:17][C:16]3=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[I-].[Mg+2].[I-].[O:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[C:10]([CH:15]3[C:16](=[O:21])[CH:17]4[CH:18]([CH:26]5[O:25][CH:29]4[CH:28]=[CH:27]5)[C:19]3=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

반응물 3

HCID 8029Furan

HCID 5462737Magnesium diiodide

HCID 595845932-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dione

생성물 1

HCID 685659594-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-10-oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dione

실험 절차

To a stirred solution of 2-[5-(4-chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dione (248 mg, 0.78 mmol) in furan (3 ml) is added magnesium iodide (44 mg, 0.15 mmol) and the reaction allowed to stir at room temperature for 4 days. The crude reaction mixture is purified by flash chromatography to give 4-[5-(4-chloro-phenyl)-2-ethyl-thiophen-3-yl]-10-oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dione as a white solid (180 mg).