反应详情

Stir a solution of 2-(2,5-bis-methoxymethoxy-3-methoxymethyl-phenyl)-cyclopent-1-enecarboxylic acid methyl ester (1.76 g, 4.80 mmol) in EtOH (75 mL, pre-filtered through a plug of basic alumina) for 1 minute with activated carbon, then filter through Celite®. Add 10% Pd/C (50% wet, 0.83 g) to the filtrate and hydrogenate this mixture at 55-60 psi for at least 20 hours. Filter the reaction through Celite® and concentrate the filtrate to afford the subtitled product (1.20 g, 68%) as an oil that may be used without further purification. 1H NMR (CDCl3) δ 1.63-1.74 (m, 1H), 1.92-2.10 (m, 4H), 2.11-2.20 (m, 1H), 3.20-3.27 (m, 4H), 3.40 (s, 3H), 3.46 (s, 3H), 3.60 (s, 3H), 3.69-3.78 (m, 1H), 4.44-1.53 (m, 2H), 4.95-5.01 (m, 2H), 5.08-5.14 (m, 2H), 6.80 (d, J=3.0 Hz, 1H), 6.94 (d, J=3.0 Hz, 1H).

1. filtrationpre-filtered through a plug of basic alumina) for 1 minute with activated carbon
2. filtrationfilter through Celite®
3. additionAdd 10% Pd/C (50% wet, 0.83 g) to the filtrate and hydrogenate this mixture at 55-60 psi for at least 20 hours
4. filtrationFilter
5. customthe reaction through Celite®
6. concentrationconcentrate the filtrate