Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1Komponenten
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (4-methoxy-2-nitrophenyl)acetic acid (400 mg; 1.9 mmol; 1 eq) in THF (10 mL) at 0° C. is added slowly under nitrogen borane-tetrahydrofuran complex (4.74 mL; 1 M; 4.7 mmol; 2.5 eq) and the reaction is stirred overnight at room temperature. No conversion is observed. The reaction mixture is heated at 70° C. for 2 h. The reaction is quenched by addition of water and the expected product is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent removed under reduced pressure. The residue obtained is purified by the flash chromatography using cyclohexane/EtOAc (7/3) as eluent to afford 350 mg (94%) of the title compound as a yellow oil. 1H NMR (CDCl3) δ 7.20 (d, J=3.0 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 6.85 (dd, J=8.0, 3.0 Hz, 1H), 3.66 (t, J=9.0 Hz, 2H), 3.61 (s, 3H), 2.86 (t, J=9.0 Hz, 2H), 1.88 (br s, 1H). HPLC (max plot) 100%; Rt 2.48 min.
Aufarbeitung
- temperatureThe reaction mixture is heated at 70° C. for 2 h
- customThe reaction is quenched by addition of water
- extractionthe expected product is extracted with EtOAc
- dry with materialThe organic phase is dried over MgSO4
- customthe solvent removed under reduced pressure
- customThe residue obtained
- customis purified by the flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-30011162150b4012ad75e34acfb79ea2
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08614215B2
Verknüpfte Notizen
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