Sodium Iodide → HCID 22100480, compound

Participants

Reaction Conditions

Reaction Steps

44 g (300 mmol) of sodium iodide and 38 ml (300 mmol) of chlorotrimethylsilane were added to 19.6 g (50 mmol) of 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanol in 120 ml of acetonitrile. The temperature rose temporarily to 32° C. After the mixture had been stirred at about 25° C. for three hours, it was poured into ice/water, decolorized with concentrated sodium bisulfite solution and extracted several times with methylene chloride. The combined organic solutions were washed with water, dried and evaporated and the residue was chromatographed over a silica gel column using methylene chloride/ethyl acetate 95:5. The 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxychroman was obtained as an oil.

Provenance & Evidence