Sodium borohydride → methyl 3-hydroxy-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoate

Participants

Reaction Steps

To a 25 mL RB flask fitted with magnetic stirrer was charged 4 mL of MeOH to the stirred solvent was added methyl 3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-3-oxopropanoate (0.08 g, 0.178 mmol) and Sodium borohydride (0.008 g, 1.21 mmol) was added 0° C. Then it was stirred at RT for 6 h, after completion of the reaction (reaction monitored by TLC), reaction mass quenched with Ice water and concentrated the reaction mixture and extracted with ethyl acetate. The organic layer washed with brine and dried by anhydrous Na2SO4 and evaporated to dryness, and the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent (0.04 g, Yield: 50%) 1H NMR (300 MHz, DMSO-d6): δ 7.62-7.65 (m, 2H), 7.32-7.40 (m, 5H), 7.23-7.26 (d, 2H), 6.90-6.93 (m, 4H), 5.36-5.38 (d, 1H) 5.22 (s, 2H), 4.92 (s, 2H), 4.85-4.89 (t, 1H), 4.04 (s, 3), 3.57 (s, 3H), 2.57-2.59 (d, 2H)

Provenance & Evidence