Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([CH:27]=[O:28])=[CH:26][C:21]=2[O:20][CH2:19]1.C(O)(C)C>C1COCC1.O>[O:18]1[C:22]2[CH:23]=[CH:24][C:25]([CH:27]([C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=3)[OH:28])=[CH:26][C:21]=2[O:20][CH2:19]1
A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (1.65 g, 7.1 mmol) and dry THF (15 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (2.9 mL, 7.1 mmol) and stirred for 20 min. Then a mixture of benzo[1,3]dioxole-5-carbaldehyde (0.98 g, 6.5 mmol) in dry THF (20 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (3.0 mL, 39 mmol) and added water (10 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with water (2×50 mL), dried over MgSO4 and concentrated to oil, which was purified by flash column chromatography (EtOAc/Hexane) to give benzo[1,3]dioxol-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol as an off-white solid (1.1 g, 56% yield): 1H NMR (CDCl3) δ 1.44 (t, J=7 Hz, 3H, CH2CH3), 2.11 (d, J=3 Hz, 1H, OH), 3.86 (s, 3H, OCH3), 4.07 (q, J=7 Hz, 2H, CH2CH3), 5.71 (d, J=3 Hz, 1H, CH), 5.93 (s, 2H, CH2), 6.74-6.91 (m, 6H, Ar). The product was used in the next step without further purification.
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