Sodium amide → 2-(2,3-Dimethoxyphenyl)ethenyl methyl ether

Participants

Reaction Steps

THF (15 mL) was added to a mixture of methoxymethyltriphenylphosphonium bromide and sodium amide (mfd. by Aldrich Chemical Co.; 3.0 g, 6.9 mmol) at room temperature and stirred for 15 minutes. To the resulting orange-colored suspension was added a solution of 2,3-dimethoxybenzaldehyde (997 mg, 6.00 mmol) in THF (5 mL), and stirred for 3 hours. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by the use of a silica gel column (silica gel 50 mL; hexane/ethyl acetate=1/0 to 15/1) to obtain 2-(2,3-dimethoxyphenyl)ethenyl methyl ether (808 mg, 83%) as a yellow oil.

Provenance & Evidence