HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methylbenzenesulfonic acid → 2-Cyclopenten-1-ylbenzofuran
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methylbenzenesulfonic acid | HCID 6925 | — |
| Reactant | Cyclopentanone | HCID 8452 | — |
| Reactant | Benzofuran | HCID 9223 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 2-Cyclopenten-1-ylbenzofuran | HCID 14005671 | — |
Reaction Steps
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)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08716493B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-b049d30655364497a5a6bf9973548205 |
| Source note | uspto-grants-2014_05 |