Methanol → 3-[4-(tert-Butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester

Participants

Reaction Steps

A 500 mL Parr hydrogenation bottle was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-formylphenyl]acrylic acid tert-butyl ester (18.3 g, 37.6 mmol), THF (60 mL), and methanol (120 mL). Triethylamine (2 mL) and then 5% Pd/C (5.9 g) were added. The mixture was shaken with hydrogen at 60 psi pressure for 48 h. The mixture was filtered through Celite and concentrated to an oil. This oil was purified using the Biotage medium pressure chromatography (EtOAc:hexanes 15:85) to a pale yellow oil (12.8 g, 69%). 1H NMR (400 MHz, CDCl3) δ 1.09 (s, 9H), 1.35 (s, 9H), 2.49 (t, J=7.6 Hz, 2H), 2.83 (t, J=7.6 Hz, 2H), 4.55 (s, 2H), 6.56 (dd, J=8.3, 2.4 Hz, 1H), 6.83 (d, J=2.9 Hz, 1H), 6.87 (d, J=8.3 Hz, 1H), 7.33-7.44 (m, 6H), 7.70 (dd, J=7.8, 1.5 Hz, 4H). MS (ES) m/e 508 (M+NH4).

Provenance & Evidence