Trimethylsilyldiazomethane → Diethyl 9-(1,3-benzodioxol-5-yl)-6-methoxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylate

Participants

Reaction Steps

Compound 33 (95 mg, 0.21 mmol) was dissolved in a mixture of MeOH (3 mL) and THF (6 mL). (Trimethylsilyl)diazomethane (2 M in hexanes, 0.6 mL, 1.2 mmol) was added to the solution. The mixture was stirred for 12 h at room temperature, and then concentrated in vacuo. The crude material was purified by column chromatography on silica gel using CH2Cl2 to afford 35 (97 mg, 99%) as a yellow oil. 1H NMR (CDCl3) δ 7.86 (d, 1H, H5, J=8.7 Hz), 7.26 (d, 1H, H6, J=8.7 Hz), 6.75-6.82 (m, 3H, H2′+H5′+H6′), 6.00 (AB, 2H, 3′,4′-OCH2O—, Δδ=11.7 Hz, J=1.2 Hz), 5.87 (AB, 2H, 7,8-OCH2O—, Δδ=9.0 Hz, J=1.2 Hz), 4.39 (q, 2H, OCH2CH3, J=7.2 Hz), 4.06 (s, 3H, 4-OCH3), 4.03 (q, 2H, OCH2CH3, J=7.2 Hz), 1.38, 1.04 (each t, 2×3H, 2×OCH2CH3, J=7.2 Hz); MS (EI) m/z 466 [M]+.

Provenance & Evidence