Imidazole → 4-[2-(t-Butyldimethylsiloxy)-ethoxy]-1-iodo-3,5-dimethoxybenzene

HRID 2181296Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[CH:7][C:6]=1[O:14][CH3:15].N1C=CN=C1.[C:21]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])([CH3:23])[CH3:22].O>CN(C)C=O>[O:1]([CH2:2][CH2:3][O:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([I:13])=[CH:9][C:10]=1[O:11][CH3:12])[Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(2-hydroxyethoxy)-1-iodo-3,5-dimethoxybenzene (2.76 g, 8.52 mmol) synthesized by the process shown in Reference Example 5 in dimethylformamide (25 mL) were added imidazole (1.16 g, 17.0 mmol) and t-butylchlorodimethylsilane (1.61 g, 10.7 mmol), and the mixture was stirred at 50° C. for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate-hexane (1:1). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 4-[2-(t-butyldimethylsiloxy)-ethoxy]-1-iodo-3,5-dimethoxybenzene as a colorless oil (3.56 g, yield: 95%).

Workup

extractionthe mixture was extracted with ethyl acetate-hexane (1:1)
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-f21f754e6bbe44d2becf917c806e5912
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890940B2

Reaction notes

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