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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2385248Erstellt: 25. Oktober 2026

Cesium carbonate → 6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

https://huagongshe.com/reaction/2385248

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
Edukt(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 7033050—
Edukt6-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 46194050—
LösungsmittelMethyl Ethyl KetoneHCID 6569—
Produkt6-bromo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 59352333101,7%

Reaktionsschritte

To a stirred solution of 6-bromospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.3 g, 4.3 mmol) in 2-butanone (40.0 mL) was added cesium carbonate (4.2 g, 12.9 mmol) and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (1.4 g, 5.4 mmol). The reaction was refluxed for 16 h, filtered and concentrated in vacuo to dryness. The residue was purified by flash chromatography with 25% ethyl acetate in hexanes to afford 6-bromo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (1.75 g, 100%) as a colorless solid: MS (ES+) m/z 400.0 (M+1), 402.0 (M+1).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08263606B2
Quelldatensatzuspto-grants-2012_09
ORD IDord-cf0b3114a8b5443f80ce562c43cc6f42
Quellennotizuspto-grants-2012_09