Ammonium Hydroxide → HCID 51358271, compound

Participants

Reaction Steps

(Methoxymethyl) triphenylphosphonium chloride (12.5 g, 36.5 mmol) was dissolved in THF (80 mL), and tBuOK (4.10 g, 36.5 mmol) and methyl 4-formylbenzoate (3.0 g, 18.3 mmol) dissolved in THF (20 mL) were added thereto while cooling with ice, followed by stirring at room temperature for 16 hours. Water was added to the resulting mixture, and after extraction with ethyl acetate, the residue was purified using medium pressure flash column chromatography (silica gel; ethyl acetate:hexane=1:8), thereby giving a mixture of (E)- and (Z)-methyl 4-(2-methoxyvinyl)benzoate (2.98 g) as an oil. The obtained mixture was dissolved in a mixture of dioxane (60 mL) and water (60 mL), and N-bromosuccinimide (3.04 g, 17.1 mmol) was added thereto at −10° C., followed by stirring for 5 minutes, and further stirring at room temperature for 1 hour. Thiourea (1.18 g, 15.5 mmol) was added to the mixture, followed by stirring at 80° C. for 1.5 hours. Ammonia aqueous solution (6 mL) was added to the resulting mixture to stop the reaction, and after stirring for 1 hour, the precipitate was collected by filtration, thereby giving the title compound (2.80 g, 65% for 2 steps) as a white solid.

Provenance & Evidence