Sodium Hydroxide → HCID 118292793, compound

Participants

Reaction Steps

An aqueous sodium hypochlorite solution (5%, 1081 g) was added dropwise to a solution of (E)-1-(3-(benzyloxy)phenyl)-N-hydroxymethanimine (150 g) and dimethyl 2-methylenesuccinate (104 g) in THF (1500 mL) at 5 C (internal temperature: 30 C or lower) over 1 hour, and then, the obtained mixture was stirred at 5 C for 1 hour. To the reaction mixture, methanol (750 mL) was added, and then, a 2 M aqueous sodium hydroxide solution (750 mL) was added dropwise at 5 C (internal temperature: 20 C or lower) over 40 minutes. The obtained mixture was gradually warmed to room temperature and stirred overnight at room temperature. The reaction mixture was concentrated into half the volume under reduced pressure, and then, water (5000 mL) and ethyl acetate (1500 mL) were added to the residue. The aqueous layer was washed with ethyl acetate (1500 mL), then 6 M hydrochloric acid (250 mL) was added thereto, and the obtained mixture was subjected to extraction with ethyl acetate (1500 mL×2). The extract was washed with brine (1500 mL) and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was washed with diethyl ether (10 mL) and hexane (1000 mL) to obtain the title compound (217 g).

Provenance & Evidence