Sodium borohydride → 1-(3-Methoxy-4-propoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanediol

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To a solution of 1-(3-methoxy-4-propoxy-5-nitrophenyl)-4-(3,4,5 -trimethoxyphenyl)-butane-1,4-dione (11.53 g, 25 mmol) in 350 mL of methanol and 250 mL of tetrahydrofuran was added dropwise a solution of sodium borohydride (3.076 g, 81.34 mmol) in 140 mL of water. After the addition was completed, the mixture was stirred at room temperature for 3 hours, quenched with water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and evaporated to provide a foam (11.53 g, 99.24%). 1H NMR (CDCl3): 1.05 (t, 3H), 1.80-1.95 (m, 6H), 3.80-3.98 (m, 12H), 4.1 (t, 2H), 4.72. (m, 2H), 6.6 (s, 2H), 7.15 (s, 1H), 7.35 (s, 1H).

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