Imidazole → 3-(3-Methoxypropoxy)4-[(triisopropylsilyl)oxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask, 4-hydroxy-3-(3-methoxypropoxy)benzaldehyde (10 g, 47.6 mmol) was introduced. DMF (69 mL) was added. The solution was cooled to 0° C. and imidazole (8.09 g, 118.9 mmol), followed by triisopropylsilyl chloride (10.7 mL, 49.9 mmol) were added. The mixture was stirred for 2 hrs and the solvent was evaporated. A saturated aqueous ammonium chloride was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 9/1) to yield 12 g (69%) of the desired product as a yellow oil.

Provenance & Evidence