Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentene-1-carboxylate → Methyl 2-[3-(2-tert-butylsilyloxypropan-2-yl)-2,5-bis(methoxymethoxy)phenyl]cyclopentane-1-carboxylate

Participants

Reaction Steps

Filter a solution of 2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-2,5-bis-methoxymethoxy-phenyl]-cyclopent-1-enecarboxylic acid methyl ester (0.715 g, 1.53 mmol) in EtOH (40 mL) through a 1×6 cm pad of activated carbon. Add the filtrate to a Pair® bottle containing 10% Pd/C (50% wet, 0.15 g) and hydrogenate this mixture at 55-60 psi for 3 hours. Filter the reaction through Celite® and concentrate the filtrate to afford the subtitled product (0.605 g, 84%) as an oil that may be used without further purification. 1H NMR (CDCl3) δ 0.10 (s, 3H), 0.11 (s, 3H), 0.94 (s, 9H), 1.60-1.67 (m, 1H), 1.91-2.04 (m, 4H), 2.11-2.18 (m, 1H), 3.22 (s, 3H), 3.17-3.24 (m, 1H), 3.45 (s, 3H), 3.58 (s, 3H), 3.65-3.72 (m, 1H), 4.79 (s, 2H), 4.95 (dd, J=5.8, 6.8 Hz, 2H), 5.10 (dd, J=6.6, 9.6 Hz, 2H), 6.74 (d, J=3.0 Hz, 1H), 7.04 (d, J=3.0 Hz, 1H).

Provenance & Evidence