Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Ethanol → 6-Chloro-1,2,3,4-tetrahydrocarbazole
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Ethanol | HCID 702 | — |
| 반응물 | Cyclohexanone | HCID 7967 | — |
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| 반응물 | N-Benzhydrylidene-N'-(4-chlorophenyl)hydrazine | HCID 9948495 | — |
| 용매 | Diethyl Ether | HCID 3283 | — |
| 생성물 | 6-Chloro-1,2,3,4-tetrahydrocarbazole | HCID 326615 | 91% |
반응 단계
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).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US06465693B2 |
| 출처 데이터셋 | uspto-grants-2002_10 |
| ORD ID | ord-b5cc02631fb3440894aa78e21145b097 |
| 출처 메모 | uspto-grants-2002_10 |