HCID 86596231, compound → HCID 68867534, compound

Participants

Reaction Steps

The 3-(3-benzyloxy-phenyl)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester (9.03 g, 15.8 mmol) was combined with 10% Pd/C (9.0 g) in ethyl acetate (200 mL). The mixture was purged with N2 then H2 and then stirred at room temperature under a H2 balloon for approximately 48 h. The reaction mixture was filtered through hyflo to remove the catalyst and the resultant filtrate dried (MgSO4). The solvent was removed in vacuo to give crude product that was purified by flash chromatography using 3:1 hexanes:acetone to afford 1.96 g (32%) 3-(3-hydroxy-phenyl)-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester. The racemic phenol was purified by preparative chiral HPLC (Chiralcel OD, 5×37 cm, 95:5 heptane:IPA mobile phase, 150 ml/min, 285 nm, GK8-A015150-031). Rf=0.32 (1:1 hexanes:acetone). 1 NMR. MS (ES−) Calc'd for C19H18O4F3 (M−1) 367. Found m/z 367 (100%).

Provenance & Evidence