PMGB

(E)-Ethyl 3-(2-chlorophenyl)acrylate (1.5 g, 0.007 mol) was dissolved in 15 mL of anhydrous dichloromethane, cooled to -78 ^oC and treated with a solution of di-iso-butylaluminum hydride (1.0 M solution in hexane, 21.4 mL, 0.021 mol) over a period of 20 minutes (the solution turned yellow in color). After 1.5 hours total at -78 ^oC, the reaction was quenched with methanol (15 mL) at -78 ^oC (the solution became colorless and then a white solid precipitated out), warmed to 23 ^oC (over 9 hrs) and treated with a saturated aqueous solution of NH₄Cl (60 mL). The resulting mixture was extracted with dichloromethane (2 × 100 mL) (emulsion formed was filtered over Celite to remove white gummy precipitate). The combined extracts were dried (Na₂SO₄) and concentrated under vacuum to give (E)-3-(2-chlorophenyl)prop-2-en-1-ol which was purified by column chromatography (silica gel, 0-50% ethyl acetate in hexanes) as a pale brown oil (0.45 g, 37% yield, NMR complies). 0.8 g of starting ester was also recovered. Ref: WO2005/097744