Ethanol → ((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oxime

Participants

Reaction Steps

[(R)-2-(2,2-Diethoxyethoxy)-4-pentenyloxymethyl]benzene (20.0 g) was dissolved in formic acid (160 ml) and water (40 ml), and the mixture was stirred at room temperature for 30 minutes. Next, water (161 ml) and ethanol (400 ml) were added, and then hydroxylamine sulfate (6.38 g) and sodium acetate (8.82 g) were added, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the insoluble matter was dissolved. Then, the excess of ethanol was evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (13.7 g).

Provenance & Evidence