4-(Benzyloxy)-3-methoxybenzaldehyde → 3-(4-Benzyloxy-3-methoxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester

Beteiligte Stoffe

Reaktionsschritte

A solution of 4-benzyloxy-3-methoxy-benzaldehyde (0.44 g, 1.92 mmol) and methyl methoxyacetate (0.19 mL, 1.92 mmol) in THF (10 mL) at −78° C. was added dropwise to sodium bis(trimethylsilyl)amide (20 mL, 2.11 mmol, 1N in THF) at −78° C. The reaction mixture was stirred for 3 h and quenched with 1N HCl (5 mL). The mixture was allowed to warm to room temperature, diluted with water (15 mL), and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 1:1) to produce 3-(4-benzyloxy-3-methoxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester as an oil (350 mg, 52%); 1H-NMR (200.15 MHz, CDCl3): δ 7.45–7.20 (m, 5H), 6.9 (s, 1H), 6.8 (b, 2H), 5.1 (s, 2H), 4.90–4.80 (m, 1H), 4.10 (m, 1H), 3.90 (s, 3H), 3.65 (s, 3H), 3.31 (s, 3H), 3.10–2.96 (m, 1H).

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