Trimethyl orthoformate → 6-tert-Butyl-4-(1,1-dimethoxyethyl)-2-iodoanisole

Participants

Reaction Steps

Methanol (6 mL), trimethyl orthoformate (262 mg, 2.4 mmol), and p-toluenesulfonic acid monohydrate (TsOH.H2O) (38 mg, 0.2 mmol) were added to 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)ethanone (664 mg, 2 mmol), and this was stirred at room temperature for 2 hours, and then at 60° C. for 1 hour. After stirring for another 3 hours at 0° C., potassium carbonate (138 mg, 1.0 mmol) was added, and after stirring for 1.5 hours on ice, the reaction solution was concentrated to dryness. Water (5 mL) and toluene (10 mL) were added to this residue and the solution was separated. The organic layer was washed with water (5 mL) and the solvent was distilled off (50° C.) to obtain 708 mg of the subject compound as pale brown crystals (yield: 93.6%).

Provenance & Evidence