2-Methylbenzenesulfonic acid → 2-Cyclopenten-1-ylbenzofuran

반응식

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.[C:15]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C1(C)C(S(O)(=O)=O)=CC=CC=1>CCOCC.C1(C)C=CC=CC=1>[C:15]1([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[CH2:19][CH2:18][CH2:17][CH:16]=1

참가 물질

실험 절차

Benzofuran was treated with butyllithium in ether followed by cyclopentanone. The resulting alcohol was dehydrated with toluenesulfonic acid in toluene to afford 2-cyclopenten-1-ylbenzofuran. Treatment with maleimide gave a cycloadduct which was aromatized by treatment with tetrachloroquinone. 1H NMR (DMSO-d6) δ 11.29 (s, 1H), 8.60 (d, 1H), 7.82 (d, 1H), 7.66 (t, 1H), 7.52 (t, 1H), 3.23 (m, 4H), 2.30 (quintet, 2H). MS m/e 276 (M−H)−.