Sodium Methoxide → 2-(4-Hydroxy-phenyl)-4-methoxy-benzofuran-5-ol
Reaktionsgleichung
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18].[CH3:19][O-:20].[Na+]>CN(C=O)C.[Cu]Br>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:18])=[C:2]([O:20][CH3:19])[C:7]=3[CH:8]=2)=[CH:12][CH:13]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
A solution of 4-bromo-2-(4-Hydroxyphenyl)-benzofuran-5-ol 130 (0.100 g, 0.32 mmol) and copper (I) bromide (0.047 g, 0.32 mmol) in DMF (4 mL) was treated with sodium methoxide (0.73 mL, 3.2 mmol, 25% by weight in MeOH) and heated at 150° C. for three hours under a nitrogen atmosphere; The reaction was quenched at room temperature with 1 N HCl and extracted with ethyl acetate (3×). The combined organic extracts were washed once with a saturated sodium bicarbonate solution, then dried over magnesium sulfate and filtered. Then the material was purified by column chromatography using 30% ethyl acetate in hexane as the eluent to yield 132 (0.030 g, 36.6%) as a brown solid: Mp. 165–1.68° C.; 1H NMR (DMSO-d6) δ 7.72 (d, 2 H, J=8.6 Hz), 7.23 (s, 1 H), 7.1 (d, 1H J=8.7 Hz), 6.86 (d, 2 H, J=8.6 Hz, 6.76 (d, 1 H, J=8.6 Hz), 3.94 (s, 3 H); MS 257 (M+H)+.
Aufarbeitung
- customThe reaction was quenched at room temperature with 1 N HCl
- extractionextracted with ethyl acetate (3×)
- washThe combined organic extracts were washed once with a saturated sodium bicarbonate solution
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customThen the material was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-c78a2f8632cd4140ab0be268093e26fa
- Quelldatensatz
- uspto-grants-2006_04
- Patentnummer
- US07022733B2
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