Reaction Steps
To a solution of crude 6-(6-formyl-2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxole-5-carbaldehyde (265 mg, 0.77 mmol) in methanol (7 mL) was added sodium borohydride (80 mg, 2.1 mmol) and the solution was stirred at room temperature for 1 hour. Water (30 mL) and ethyl acetate (30 mL) were then added to the reaction, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined extracts were dried over Na2SO4 and filtered. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (40 g), eluting with hexane-ethyl acetate (1:2), followed by crystallisation (ethyl acetate), which yielded (6-(6-(hydroxymethyl)-2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxol-5-yl)methanol as a white solid (230 mg, 86%); m.p. 123-124° C.; High Resolution Mass Spectrometry Found: M+Na+ 371.1105 (C18H20O7Na requires 371.1107); NMR Spectrum δH (300 MHz, CDCl3) 7.00 (2H, s, 7-H), 6.88 (1H, s, 4-H), 6.63 (1H, s, 5′-H), 6.04 (2H, s, 2-H), 4.30 (2H, m, CH2OH), 4.21 (2H, m, CH2OH), 3.93 (3H, s, OCH3), 3.91 (3H, s, OCH3), 3.62 (3H, s, OCH3); NMR Spectrum δC (75 MHz, CDCl3) 56.4, 61.4, 61.5 (CH2), 63.1 (CH2), 63.7, 101.7, 108.7, 110.4, 110.6, 126.6, 129.1, 133.8, 135.5, 142.0, 147.5, 147.8, 151.4, 153.5; νmax/cm−1 (thin film) 3254, 2944, 2889, 1603, 1480, 1410, 1328, 1235, 1146, 1111, 1033, 928; m/z (ES) 412 (MNa2H2O+, 100%), 371 (MNa+, 60); Rf(hexane-ethyl acetate 1:2) 0.14.
