3-Benzyloxypropyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylate → 3-Hydroxypropyl 9-(1,3-benzodioxol-5-yl)-8-methyl-benzo[g][1,3]benzodioxole-7-carboxylate

Participants

Reaction Steps

A mixture of 6 (48 mg, 0.079 mmol) and 10% Pd/C (12 mg) in dry THF (5 mL) was stirred for 14 h at room temperature under 1 atm of hydrogen. The mixture was filtered, and the filtrate evaporated at reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (40:1, v/v) to yield 7 (30 mg, 93%) as a yellow oil. 1H NMR (CDCl3) δ 8.32 (s, 1H, H4), 7.50 (d, 1H, H5, J=8.7 Hz), 7.18 (d, 1H, H6, J=8.7 Hz), 6.87 (d, 1H, H5′, J=7.8 Hz), 6.72 (d, 1H, H2′, J=1.5 Hz), 6.68 (dd, 1H, H6′, J=1.5, 7.8 Hz), 6.05 (AB, 2H, 3′,4′-OCH2O—, Δδ=9.6 Hz, J=1.5 Hz), 5.83 (AB, 2H, 7,8-OCH2O—, Δδ=1.5 Hz, J=1.5 Hz), 4.54 (t, 2H, 3-COOCH2(CH2)2OH, J=6.3 Hz), 3.83 (t, 2H, 3-COO(CH2)2CH2OH, J=6.3 Hz), 2.34 (s, 3H, 2-CH3), 2.06 (quintet, 2H, 3-COOCH2CH2CH2OH, J=6.3 Hz); MS (EI) m/z 408 [M]+.

Provenance & Evidence