Imidazole → 2-(4-Hydroxy-phenyl)-7-imidazol-1-ylmethyl-benzofuran-5-ol

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Reaktionsgleichung

Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[C:5]([OH:19])[CH:4]=1.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.O>CN(C=O)C>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[O:10][C:11]3[C:3]([CH2:2][N:20]4[CH:24]=[CH:23][N:22]=[CH:21]4)=[CH:4][C:5]([OH:19])=[CH:6][C:7]=3[CH:8]=2)=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of benzyl bromide 4 (0.070 g, 0.215 mmole) in 10 mL DMF was added imidazole (0.030 g, 0.437 mmole). After stirring at 60° C. for 3 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 9:1) to afford 0.059 g (88%) of imidazole 16 as a light tan solid: Mp=269–271° C.; 1H NMR (DMSO-d6) δ 9.88 (s, 1 H), 9.24 (s, 1 H), 7.88 (s, 1 H), 7.72 (d, 2 H, J=8.6 Hz), 7.26 (s, 1 H), 7.04 (s, 1 H), 6.93 (s, 1 H), 6.88 (d, 2 H, J=8.7 Hz), 6.83 (d, 1 H, J=2.3 Hz), 6.50 (d, 1 H, J=2.3 Hz), 5.46 (s, 2 H); MS 305 (M−H)−

Aufarbeitung

extractionextracted with ethyl acetate
washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
dry with materialdried with magnesium sulfate
concentrationThe organic phases were concentrated
customchromatographed with silica gel (hexanes:ethyl acetate, 9:1)

Quellen und Nachweise

ORD-Eintrag: ord-294958d3c0bc4d60af6c9fef38574e35
Quelldatensatz: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07022733B2

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