Water → HCID 59587910, compound

Participants

Reaction Steps

To a solution of 4-methoxybenzyl-3-pyrroline (3.0 g, 15.8 mmol) in methanol (12 ml) cooled at 0° C., water was added (3 ml) and H2SO4 96% (1.0 ml, 19.0 mmol). The solution was stirred for 10 min. and 3-chloroperoxybenzoic acid (5.0 g, 20.5 mmol) was added in portions. The suspension was stirred at room temperature for 18 hours. Methanol was evaporated, water (15 ml) was added and the aqueous solution was neutralized with aq. NaOH 20% until pH=7. The suspension was extracted with dichloromethane and the organic phase was washed with saturated solution of NaHCO3, water and saturated solution of NaCl, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography: silica gel, gradient hexane:ethyl acetate (1:1) to neat ethyl acetate to give the titled compound (1.92 g, 59% yield) as yellow oil.

Provenance & Evidence