Water → 3,4-Dimethoxyphenylethanolamine

Participants

Reaction Steps

3,4-dimethoxybenzaldehyde (2.00 g, 12.04 mM) and trimethylsilyl cyanate (1.57 g, 15.04 mM) were dissolved in dry methylene chloride (1 ml). While stirring at room temperature, zinc iodide (8.5 mg) was carefully added and the mixture was stirred for 2 hours. Next, the solution was dropwise added to a solution of lithium aluminum hydride (1.10 g, 28.88 mM) in dried tetrahydrofuran (120 ml) cooled to 0° C., then the reaction temperature was gradually warmed to room temperature and the mixture was stirred for 1 hour. Water (2 ml) was carefully added while cooling the reaction solution in an ice bath, the mixture was stirred for 1 hour, then the solution was filtered through Celite. The filtrate was dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo to obtain a crude product (2.37 g) as a yellow solid. The crude product thus obtained had a sufficient purity even without purification, so could be used for the next reaction as it was.

Provenance & Evidence