57371-44-5

To a stirred suspension of anhydrous tetrahydrofuran (THF, 10 mL) of lithium aluminum hydride (LiAlH4, 0.303 g, 7.98 mmol) was added slowly and dropwise (10 mL) of anhydrous THF solution of ethyl (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylate (25a, 0.85 g, 3.19 mmol) at 0 °C. The reaction mixture was subsequently refluxed for 4 h, cooled to 0 °C, diluted with ether and the reaction was quenched by dropwise addition of saturated aqueous sodium sulfate (Na2SO4). Solid impurities were removed by filtration and washed several times with hot ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate (Na2SO4). After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether, 3:7) to afford pure 3-(4-(benzyloxy)-3-methoxyphenyl)propan-1-ol (26a, 0.628 g, 87% yield) as a viscous liquid.

[1] European Journal of Organic Chemistry, 2015, vol. 2015, # 33, p. 7344 - 7351
[2] Tetrahedron Asymmetry, 2011, vol. 22, # 24, p. 2124 - 2133
[3] Patent: US6211215, 2001, B1