HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 61860Erstellt: 24. Oktober 2026
Triphenylphosphine → 7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
https://huagongshe.com/de/reaction/61860
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triphenylphosphine | HCID 11776 | — |
| Edukt | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Edukt | (R)-Solketal | HCID 736056 | — |
| Edukt | 7-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile | HCID 66835270 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | 7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile | HCID 66834531 | — |
Reaktionsschritte
Under nitrogen atmosphere, 7-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound W3, 15 mg, 0.05 mmol) and triphenylphosphine (40 mg, 3 eq.) were added with THF (1 ml), further added dropwise with ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (20 mg, 3 eq.) and 2.19 N toluene solution of diethyl azodicarboxylate (68 μL, 3 eq.), and the mixture was stirred at 50° C. for 2 hr. After cooling, the reaction solution was added with ethyl acetate, washed with brine, dried over sodium sulfate, and filtered. The residues obtained after concentration under reduced pressure were purified by preparative TLC (ethyl acetate/dichloromethane), and the resulting solid was washed with dichloromethane to obtain the target compound (brown powder, 5 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09440922B2 |
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| Quelldatensatz | uspto-grants-2016_09 |
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| ORD ID | ord-4b8e140ba2db4cb3834f3c390b3c7ae3 |
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| Quellennotiz | uspto-grants-2016_09 |
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