Hydrochloric Acid → 3-{3-[2-Hydroxy-2-(5-phenyl-furan-2-yl)-ethyl]-phenyl}-acrylic acid

Participants

Reaction Steps

To ketone (27) (33 mg; 0.10 mmol) dissolved in MeOH (2 mL) was added sodium borohydride (8 mg, 0.21 mmol). Subsequent additions of sodium borohydride (2 mg) were added until the reaction was complete. The reaction mixture was acidified to pH 5 by dropwise addition of 1N HCl and extracted with TBME (×3). The organic layer was dried (MgSO4) and the solvent concentrated in vacuo to give the title compound as a white solid. Yield: 20 mg, 61%; LC-MS tr 2.02 min; HPLC Purity: 100%; MS (ES+) m/z 335 (M+H), 317 (M−H2O+H); 1H NMR (400 MHz; CDCl3): δ 3.20-3.30 (d, 2H), 5.0 (t, 1H), 6.3 (d, 1H), 6.40 (d, 1H), 6.60 (d, 1H), 7.20-7.50 (m, 7H), 7.65-7.80 (m, 3H)

Provenance & Evidence