Reaktionsgleichung
CCO[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[CH3:12])=[O:5].[CH3:13][CH2:14][Mg+].[Br-].[CH2:17]1COC[CH2:18]1>>[CH3:12][C:7]1[C:6]([C:4]([OH:5])([CH2:13][CH3:14])[CH2:17][CH3:18])=[CH:11][CH:10]=[CH:9][N:8]=1Komponenten
Versuchsvorschrift
To a stirred solution of ethyl 2-methyl nicotinate (1.04 g, 6.30 mmol) in dry THF (30 mL) was slowly added EtMgBr (3.0 M in Et2O, 5.2 mL, 16 mmol). The mixture was warmed to reflux and stirred for 60 h under N2. The suspension was cooled, poured into ice (50 mL) and stirred for 3 h. The layers were separated, and the aqueous layer was extracted with Et2O (5×100 mL). The combined organic layers were dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2), affording 3-(2-methyl-pyridin-3-yl)-pentan-3-ol as a yellow solid (0.447 g, 40%). 1H NMR (CDCl3) δ 0.77 (t, 6H, J=7.5 Hz), 1.80-2.12 (m, 4H), 2.70 (s, 3H), 7.12 (dd, 1H, J=4.8, 7.8 Hz), 7.87 (dd, 1H, J=7.8, 1.5 Hz), 8.39 (dd, 1H, J=4.8, 1.5 Hz).
Aufarbeitung
- temperatureThe mixture was warmed
- temperatureto reflux
- temperatureThe suspension was cooled
- stirringstirred for 3 h
- customThe layers were separated
- extractionthe aqueous layer was extracted with Et2O (5×100 mL)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- filtrationAfter filtration the solvent
- customwas removed by evaporation under vacuum
- customthe residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2)
Quellen und Nachweise
- ORD-Eintrag
- ord-ca76cef1d78a4aafb01efc9473836ad7
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07863293B2
Verknüpfte Notizen
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