化工社化工社 化学情報印刷レポート · 研究参考用
Ethanol → 6-Chloro-1,2,3,4-tetrahydrocarbazole
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | Cyclohexanone | HCID 7967 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| 反応物 | N-Benzhydrylidene-N'-(4-chlorophenyl)hydrazine | HCID 9948495 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 生成物 | 6-Chloro-1,2,3,4-tetrahydrocarbazole | HCID 326615 | 91% |
反応手順
N-(4-Chlorophenyl)benzophenone hydrazone (1.0 equiv., 0.5 mmol, 153 mg), cyclohexanone (1.5 equiv., 0.75 mmol, 0.078 mL), and TsOH.H2O (2 equiv., 1.0 mmol, 190 mg) were dissolved in ethanol (3 mL) and heated to reflux for 41 hours. The reaction mixture was then cooled to room temperature, diluted with Et2O (5 mL), neutralized with a saturated NaHCO3 solution, and extracted with Et2O (3×10 mL). The organic extracts were then dried over K2CO3, filtered and concentrated under vacuum. Purification by flash column chromatography (10% EtOAc/Hex) gave the title product as a white solid (94 mg, 0.46 mmol, 91% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06465693B2 |
| 出典データセット | uspto-grants-2002_10 |
| ORD ID | ord-b5cc02631fb3440894aa78e21145b097 |
| 出典メモ | uspto-grants-2002_10 |