化工社化工社 化学情報印刷レポート · 研究参考用
2-Methylbenzenesulfonic acid → 2-Cyclopenten-1-ylbenzofuran
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2-Methylbenzenesulfonic acid | HCID 6925 | — |
| 反応物 | Cyclopentanone | HCID 8452 | — |
| 反応物 | Benzofuran | HCID 9223 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 生成物 | 2-Cyclopenten-1-ylbenzofuran | HCID 14005671 | — |
反応手順
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)−.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08716493B2 |
| 出典データセット | uspto-grants-2014_05 |
| ORD ID | ord-b049d30655364497a5a6bf9973548205 |
| 出典メモ | uspto-grants-2014_05 |