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