Cesium carbonate → 3-{2-[2-(2-{2-Azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde

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Reaction Conditions

Reaction Steps

A mixture of 5.22 g (17.55 mmol) 2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethyl methanesulfonate 7, 3.20 g (17.55 mmol) 3,4-dimethoxy-5-hydroxybenzaldehyde 1 and 11.5 g (35.20 mmol) caesium carbonate in 120 ml DMF was heated at 50° C. for 17 hrs. The mixture was poured into 100 ml saturated aqueous ammonium chloride solution and extracted with methylene chloride. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated. The residue was purified by silica gel column chromatography (toluene/ethyl acetate 1/1), yielding 4.58 g (11.95 mmol, 68%) of the product as a clear yellow oil. 1H-NMR (CDCl3) δ=9.77 (s, 1H), 7.09 (d, 1H, J=2.2 Hz), 7.06 (d, 1H, J=2.2 Hz), 4.17 (m, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 3.83 (m, 2H), 3.66 (m, 2H), 3.60 (m, 8H), 3.30 (t, 2H, J=5.4 Hz) ppm. 13C-NMR δ=190.7, 153.6, 152.7, 144.2, 131.5, 109.0, 106.4, 70.7, 70.6, 70.5 (2 signals), 69.8, 69.5, 68.8, 60.8, 56.1, 50.5 ppm. MS: m/z=383 [M]+. Anal. calcd for C17H25N3O7: C, 53.26, H, 6.57, N, 10.96. Found C, 53.15, H, 6.66, N, 10.99.

Provenance & Evidence