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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 351365Erstellt: 24. Oktober 2026

Ethyl Acetate → Ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

https://huagongshe.com/de/reaction/351365

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthyl AcetateHCID 8857—
EduktEthyl cyanoformateHCID 69336—
Edukt1,4-Dioxaspiro[4.5]decan-8-oneHCID 567415—
EduktLithium HexamethyldisilazideHCID 2733832—
LösungsmittelWaterHCID 962—
LösungsmittelTetrahydrofuranHCID 8028—
ProduktEthyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylateHCID 559688—

Reaktionsbedingungen

Temperatur-78 °C

Reaktionsschritte

1,4-Cyclohexanedione mono-ethylene ketal (25 g) was dissolved in THF and cooled to −78° C. 1M Lithium bis(trimethylsily)amide (160 mL) in THF was added dropwise. After 30 min, ethyl cyanoformate (15.9 mL) was added dropwise. After 60 min, the solution was poured into EtOAc and water containing ice. The organic layer was washed with water and brine before it was dried and concentrated. This crude was filtered through a plug of silica to give the 8-oxo-1,4-dioxa-spiro[4.5]decane-7-carboxylic acid ethyl ester (32.4 g). MS found: (M+H)+=228.9

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07183270B2
Quelldatensatzuspto-grants-2007_02
ORD IDord-61d7887e28344bd297d6736670177602
Quellennotizuspto-grants-2007_02