1,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioate → 2-(4-Bromophenyl)-2-methylpropane-1,3-diol
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:19])([CH2:14][OH:15])[CH2:9][OH:10])=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of diethyl 2-(4-bromophenyl)-2-methylmalonate (850 mg, 2.6 mmol) in dry THF (5 mL) at 0° C. was added a 1.0M solution of lithium aluminum hydride in THF (2.6 mL, 2.6 mmol). After stirring for 2 h at 0° C., the mixture was quenched by slow addition of water (5 mL). The mixture was made acidic by addition of 1N HCl and was then extracted with dichloromethane (2×20 mL). The organics were combined, dried over Na2SO4 and evaporated to give 2-(4-bromophenyl)-2-methylpropane-1,3-diol (500 mg, 79%) 1H NMR (400 MHz, DMSO-d6) δ 7.47-7.43 (m, 2H), 7.35-7.32 (m, 2H), 4.59-4.55 (m, 2H), 3.56-3.51 (m, 4H), 1.17 (s, 3H).
Aufarbeitung
- customthe mixture was quenched by slow addition of water (5 mL)
- additionThe mixture was made acidic by addition of 1N HCl
- extractionwas then extracted with dichloromethane (2×20 mL)
- dry with materialdried over Na2SO4
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-e9fabb0b936f44b6a0fe2c9c85dfa96f
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07691902B2
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