Chlorotrimethylsilane → HCID 15480784, compound

Participants

Reaction Steps

To a solution of 8-methoxy-1,4-benzodioxane-5-carbaldehyde (12 g, 62 mmol) in acetonitrile (140 mL) was added lithium bromide (12 g, 110 mmol), and then trimethylsilyl chloride (12 mL, 95 mmol) was added dropwise. After 15 minutes, the mixture was ice-cooled, and 1,1,3,3-tetramethyldisiloxane (19 mL, 110 mmol) was added dropwise, followed by stirring at room temperature for 2 hours. The mixture was diluted with dichloromethane, and then was filtered through Celite. The solvent was evaporated in vacuo to give a pale yellow oil. To a solution of the obtained crude 5-bromomethyl-8-methoxy-1,4-benzodioxane in DMF(180 mL) was added sodium cyanide (9.2 g, 190 mmol), followed by stirring at room temperature for 60 hours. To the mixture was added water under ice-cooling, and the precipitated solid was collected by filtration to give Compound 1a (6.8 g, 53%) as an ash-colored solid.

Provenance & Evidence