2,4-Hexadien-1-OL → 4,4'-Di-2,4-hexadienoxybenzophenone
Reaktionsgleichung
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19]([OH:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]>CN(C=O)C>[CH2:19]([O:25][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:7][CH2:6][CH:5]=[CH:4][CH:3]=[CH:2][CH3:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4,4'-Difluorobenzophenone (34) (4.8 grams, 22 mmol) was dissolved in anhydrous DMF (1 liter). NaH (95%; 5.6 grams, 220 mmol) was added and the solution was cooled to 0° C. 2,4-Hexadienol (5.8 mL, 51 mmol) was slowly added to the solution and the reaction mixture was allowed to warm to room temperature with stirring under argon overnight. The reaction mixture was concentrated in vacuo, dissolved in dichloromethane, and washed with water. The organic phase was dried (MgSO4) and concentrated and purified by column chromatography (silica gel; hexane/CH2Cl2, 1/3) to afford 2.07 grams (25%) of compound 35 as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.73 (d, J=6.6 Hz, 6H), 4.68 (d, J=6.0 Hz, 4H), 5.69-5.84 (m, 4H), 6.05-6.19 (m, 2H), 6.31-6.45 (m, 2H), 7.08 (d, J=9.0 Hz, 4), 7.68 (d, J=10.2 Hz, 4).
Aufarbeitung
- temperatureto warm to room temperature
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutiondissolved in dichloromethane
- washwashed with water
- dry with materialThe organic phase was dried (MgSO4)
- concentrationconcentrated
- custompurified by column chromatography (silica gel; hexane/CH2Cl2, 1/3)
Quellen und Nachweise
- ORD-Eintrag
- ord-993632ae505c479aba1aa985bf9f4bdb
- Quelldatensatz
- uspto-grants-1999_12
- Patentnummer
- US06001966
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