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

Participants

Reaction Conditions

Reaction Steps

A mixture of 3 (78 mg, 0.2 mmol) and benzyl bromide (0.38 mL, 3.2 mmol), and powdered KOH (168 mg) was heated at 140° C. for 3 h, and then cooled to room temperature. The mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The extract was washed with water (3×100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using CH2Cl2 to give 4 (56 mg, 51%) as a colorless liquid. 1H NMR (CDCl3) δ 8.27 (s, 1H, H4), 7.51 (d, 1H, H5, J=8.4 Hz), 7.23-7.44 (m, 10H, 2×OCH2Ph), 7.22 (d, 1H, H6, J=8.4 Hz), 6.82 (d, 1H, H5′, J=7.8 Hz), 6.77 (d, 1H, H2′, J=1.5 Hz), 6.71 (dd, 1H, H6′, J=1.5, 7.8 Hz), 6.05 (AB, 2H, 3′,4′-OCH2O—, Δδ=10.2 Hz, J=1.2 Hz), 5.84 (AB, 2H, 7,8-OCH2O—, Δδ=4.8 Hz, J=1.2 Hz), 5.34 (s, 2H, 3-COOCH2Ph), 4.67 (s, 2H, 2-CH2OCH2Ph), 4.32 (s, 2H, 2-CH2OBn); MS (EI) m/z 546 [M]+.

Provenance & Evidence