Efficient Role of Mg-ZnCl₂ for Selective Reduction of α,β-Unsaturated ­Carbonyl Compounds in Aqueous Medium

Abstract

A facile strategy for the convenient reduction of α,β-unsaturated carbonyl compounds and conjugated alkynes has been ­accomplished by Mg-ZnCl₂ system in aqueous medium.

α,β-unsaturated carbonyl compounds - reduction - magnesium - zinc chloride - aqueous reaction

References

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<A NAME="RD32504ST-19">19</A>

Illustrative Experimental Procedure of 1,3-Diphenyl-propan-1-one (Entry 1).
To a suspension of 1,3-diphenylprop-2-en-1-one (1.04 g, 5 mmol) in distilled H₂O (20 mL) was added magnesium turnings (1.80 g, 7.5 mmol) and ZnCl₂ (1.0 g, 7.5 mmol) under stirring. Immediately after addition, an exothermic reaction took place and the magnesium turnings were consumed giving a grey opaque mixture. After stirring for 20 min, the reaction mixture was extracted with CH₂Cl₂ (3 × 10 mL), and the combined organic extracts were washed with H₂O, dried and evaporated to give a residue which was purified by column chromatography over silica gel (EtOAc-hexane = 2:8) to afford 1,3-diphenyl-propan-1-one as an off-white solid, yield 0.19 g (94%), mp 69-70 °C. IR: 1685 cm^-1. ¹H NMR (CDCl₃): δ = 2.90 (2 H, t, J = 6.1 Hz), 3.05 (2 H, t, J = 6.1 Hz), 6.75-7.70 (10 H, m). MS (ESI): m/z = 233 [M⁺ + 23]. Anal. Calcd for: C, 85.68; H, 6.71. Found: C, 85.21; H, 6.68.

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