Hydroxyamine chloride → methyl (E)-2-[2-[[4-[(E)-C-ethyl-N-hydroxycarbonimidoyl]-2,5-dimethylphenoxy]methyl]phenyl]-3-methoxyprop-2-enoate

Participants

Reaction Steps

To a solution of 0.17 g (0.44 mmol) of (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 3 and 0.06 g (0.88 mmol) of hydroxylamine chloride in 10 mL of methanol was added 0.8 g of a molecular sieve for dehydration. The reaction mixture was stirred at room temperature for 3 hours and filtered through celite and the filtrate was concentrated in a vacuum. The concentrate was stirred in water (10 mL) and extracted twice with 10 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified through silica gel chromatography to produce (E)-methyl 2-(2-((4-((E)-1-(hydroxyimino)propyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (0.11 g, yield: 67%).

Provenance & Evidence