Methanol → 2-(2-Chloro-5-methoxy-phenyl)-propionaldehyde
Reaktionsgleichung
C[O:2][C:3](=O)[CH:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[Cl:14])[CH3:5].[H-].C([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:14][C:7]1[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=1[CH:4]([CH3:5])[CH:3]=[O:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
2-(2-Chloro-5-methoxy-phenyl)-propionic acid methyl ester (850 mg) was dissolved in toluene (40 mL) and cooled to −78° C. Diisobutylaluminium hydride (20% in toluene, 3.69 mL) was added over a period of 15 minutes. Stirring was continued for 45 minutes at −78° C. Methanol (2 mL) was added and then 1 N potassium sodium tartrate solution (10 mL). The cooling bath was removed and the mixture was allowed to warm to RT. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The title compound was obtained as a light yellow oil (710 mg) and was used without further purification. 1H-NMR (□, CDCl3): 9.72 (s, 1H), 7.34 (d, 1H), 6.79 (dd, 1H), 6.66 (d, 1H), 4.10 (q, 1H), 3.79 (s, 3H), 1.43 (d, 3H).
Aufarbeitung
- customThe cooling bath was removed
- temperatureto warm to RT
- additionThe mixture was diluted with water
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-4544ed70255a4396a4956c8154263480
- Quelldatensatz
- uspto-grants-2012_03
- Patentnummer
- US08143280B2
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