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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

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriphenylphosphineHCID 11776—
Eduktethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Edukt(R)-SolketalHCID 736056—
Edukt7-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66835270—
LösungsmittelTolueneHCID 1140—
LösungsmittelTetrahydrofuranHCID 8028—
LösungsmittelEthyl AcetateHCID 8857—
Produkt7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66834531—

Reaktionsbedingungen

Temperatur50 °C

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09440922B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-4b8e140ba2db4cb3834f3c390b3c7ae3
Quellennotizuspto-grants-2016_09