Citric Acid → 1,3-Bis(4-methoxyphenyl)-2-phenylpropane-1,3-dione
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[C:18](Cl)(=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:17])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:27])=[CH:7][CH:8]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 1-(4-methoxyphenyl)2-phenylethan-1-one (1.0 equiv.) in THF at −78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]2NLi. The solution was stirred for 1 h at −78° C., followed by addition of addition of 1.2 equiv. of p-anisoyl chloride. The reaction mixture was stirred for 10 min at −78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,3-bis(4-methoxyphenyl)-2-phenylpropane-1,3-dione.
Aufarbeitung
- stirringThe reaction mixture was stirred for 10 min at −78° C.
- waitfor 22 h at rt
- extractionextracted with EtOAc
- washThe combined organic layers were washed with water
- dry with materialdried over Na2SO4
- customRemoval of solvent in vacuo
- customprovided a crude solid which
- customwas purified by flash chromatography (CH2Cl2)
Quellen und Nachweise
- ORD-Eintrag
- ord-1531d9e8ec354efc8db8ed8529b0b84c
- Quelldatensatz
- uspto-grants-2001_09
- Patentnummer
- US06291505B1
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