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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1690702Erstellt: 25. Oktober 2026

Sodium Carbonate → 6-Nitro-5-vinyl-indan-1-one

https://huagongshe.com/reaction/1690702

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium CarbonateHCID 10340—
EduktDibutyl Vinylboronate (stabilized with Phenothiazine)HCID 236543—
Edukt5-bromo-6-nitro-2,3-dihydro-1H-inden-1-oneHCID 53485149—
KatalysatorHCID 178418476HCID 178418476—
LösungsmittelOxolane--water (1/1)HCID 21881883—
Produkt6-Nitro-5-vinyl-indan-1-oneHCID 5761848079%

Reaktionsschritte

A solution of 5-bromo-6-nitro-indan-1-one (58 mg, 0.23 mmol), (J. Med. Chem., 2003, 46, 399-408), vinylboronic acid dibutyl ester (74 μL, 0.34 mmol), Pd(PPh3)2Cl2 (7.8 mg, 0.0011 mmol), and Na2CO3 (167 mg, 1.57 mmol) in 4:1 THF/H2O (1.4 mL/360 μL) was heated to 80° C. overnight. The crude reaction was filtered over Celite and extracted with EtOAC. The organic phase was dried (MgSO4), filtered, and concentrated. The crude material was chromatographed (SiO2) to afford 36 mg (79%) of 6-Nitro-5-vinyl-indan-1-one; LC/MS calculated for [M+H]+ C11H9NO2: 204.1, found: 204.1.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08153671B2
Quelldatensatzuspto-grants-2012_04
ORD IDord-1e8c2994e86a498d92cf684018961c13
Quellennotizuspto-grants-2012_04