Acetic Acid → 3-Oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile
Reaktionsgleichung
[C:1]([CH:3]=[C:4]([O-:6])[CH3:5])#[N:2].[Na+].[O:8]=[C:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=O)[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.C(O)(=O)C.N1CCCCC1>ClCCl>[O:6]=[C:4]([CH3:5])[C:3](=[CH:22][C:17]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:8])[C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:1]#[N:2]Komponenten
Versuchsvorschrift
The compound from example 11A (5.21 g, 25.0 mmol) is introduced into 180 ml of dichloromethane, and the compound from example 20A (2.89 g, 27.5 mmol), acetic acid (1.72 ml, 30.0 mmol) and piperidine (0.25 ml, 2.50 mmol) are added. The mixture is stirred at the boiling point with a water trap for 4 h. Cooling to RT is followed by dilution with 30 ml of dichloromethane and washing with water (2×50 ml), the organic phase is dried over sodium sulfate and the solvent is removed in a rotary evaporator. The resulting crude product is purified by chromatography on silica gel 60 with dichloromethane as mobile phase. Combining the product fractions and removing the solvent results in 5.40 g (79% of theory) of the title compound as mixture of E/Z isomers.
Aufarbeitung
- washwashing with water (2×50 ml)
- dry with materialthe organic phase is dried over sodium sulfate
- customthe solvent is removed in a rotary evaporator
- customThe resulting crude product is purified by chromatography on silica gel 60 with dichloromethane as mobile phase
- customremoving the solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-bdae7f54926e42d1a67f1fdf84f4d451
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08404709B2
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