Reaktionsgleichung
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:7]([OH:11])=[CH:8][C:9]=1[CH3:10])[CH:5]=O.C([O-])([O-])=O.[K+].[K+].[F:19][C:20]([F:29])([F:28])/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]2[C:7](=[CH:8][C:9]=1[CH3:10])[O:11][CH:21]([C:20]([F:19])([F:29])[F:28])[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a solution of 3-chloro-6-hydroxy-2,4-dimethylbenzaldehyde (6.9 g, 37.4 mmol) in 80 mL of DMF was added dried finely powdered K2CO3 (11.36 g, 82.2 mmol). With mechanical stirring, the reaction was heated to 65° C. To the suspension was added dropwise ethyl trifluorocrotonate (7.54 g, 44.9 mmol). The stirring reaction was heated at 90° C. for 1.5 h. K2CO3 was filtered from the cooled reaction. From the reaction under vacuum, DMF was removed. The resulting residue was dissolved in 400 mL EtOAc. The organic solution was washed with 100 mL 1 M KHSO4, 70 mL of satd. KHCO3, 100 mL brine, followed by drying over MgSO4, and concentrating under vacuum. The crude desired product (13.8 g) of was isolated. After employing flash chromatography conditions, pure compound (9.8 g, 78%) of was isolated and its structure confirmed by NMR and LC-MS.
Aufarbeitung
- customThe stirring reaction
- temperaturewas heated at 90° C. for 1.5 h
- filtrationK2CO3 was filtered from the cooled reaction
- customFrom the reaction under vacuum, DMF
- customwas removed
- dissolutionThe resulting residue was dissolved in 400 mL EtOAc
- washThe organic solution was washed with 100 mL 1 M KHSO4, 70 mL of satd
- dry with materialby drying over MgSO4
- concentrationconcentrating under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-42540ae1ea6d43768d62b998090f1aae
- Quelldatensatz
- uspto-grants-2007_08
- Patentnummer
- US07259266B2
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