Sodium hydride → 1-(4-Formylphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene
Reaktionsgleichung
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[H-].[Na+].F[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1>CN(C=O)C>[CH:29]([C:28]1[CH:31]=[CH:32][C:25]([O:1][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[CH:5]=[CH:4][C:3]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:26][CH:27]=1)=[O:30]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
A solution was prepared of 9.8 g (35 mmol) of 1-hydroxy-2-(3-methoxyphenyl)-6-methoxynaphthalene in 490 mL of DMF under a nitrogen atmosphere and to this solution was slowly added 1.47 g (36.8 mmol) of 60% NaH in mineral oil. After ten minutes, 7.5 mL (70 mmol) of 4-fluorobenzaldehyde was added and the reaction mixture was heated to 70° C. for sixty-four hours. The reaction mixture was evaporated to dryness and the residue partitioned between water and EtOAc. The EtOAc layer was dried with Na2SO4 and chromatographed on a silica gel column eluted with EtOAc-hexane (1:9)(v/v). The final product was further purified by crystallization from MeOH. This yielded 2.4 g of the title compound as a tan solid, mp 145-146° C.
Aufarbeitung
- waitAfter ten minutes
- customThe reaction mixture was evaporated to dryness
- customthe residue partitioned between water and EtOAc
- dry with materialThe EtOAc layer was dried with Na2SO4
- customchromatographed on a silica gel column
- washeluted with EtOAc-hexane (1:9)(v/v)
- customThe final product was further purified by crystallization from MeOH
Quellen und Nachweise
- ORD-Eintrag
- ord-235c5b4a460442f5809204c552a2c8b4
- Quelldatensatz
- uspto-grants-2004_11
- Patentnummer
- US06812244B2
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