Reaktionsgleichung
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]#[N:20])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:23])[C:9]([O:21]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1>>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]#[N:20])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:23])[C:9]([OH:21])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]Komponenten
Reaktionsbedingungen
- Temperatur
- 200 °C
Versuchsvorschrift
A mixture of 9a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (65 mg) and pyridine hydrochloride (4.2 g) was heated in an oil bath at 200° C. for 85 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates, developing with 5% MeOH in CH2Cl2. The product bands were eluted with 10% MeOH in CH2Cl2, the eluant evaporated under vacuum, and the residue lyophilized from benzene (3 mL) plus EtOH (0.1 mL) to afford 9a-butyl-8-chloro-4-cyano-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous yellow solid.
Aufarbeitung
- temperatureAfter cooling to room temperature
- customthe mixture was partitioned between EtOAc (50 mL) and water (50 mL)
- washThe organic phase was washed with brine (20 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under vacuum
- customThe residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates
- washThe product bands were eluted with 10% MeOH in CH2Cl2
- customthe eluant evaporated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-4492a1316c2143eaaae289f2e539a4d5
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07087599B2
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