Methyl 4-(benzyloxy)-3-(5,5-dimethylcyclopent-1-enyl)benzoate → Methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate

Participants

Reaction Steps

To a flask containing 66.11D (3.03 g, 9.0 mmol) in MeOH (25.0 mL) was added palladium, 10% wt. on activated carbon (0.48 g, 0.45 mmol). After purging, the mixture was stirred under an atmosphere of hydrogen at room temperature. The reaction was monitored with TLC and LC-MS. After 27.5 hours, the reaction was filtered through Celite. After concentration, the residue was purified on silica gel using 0-50% EtOAc in hexanes to yield 66.11E as a colorless oil that solidified (1.99 g, 89%). 1H NMR (400 MHz, CDCl3) δ ppm 7.91 (1H, d, J=2.3 Hz), 7.79 (1H, dd, J=8.4, 2.2 Hz), 6.82 (1H, d, J=8.2 Hz), 5.54 (1H, s), 3.90 (3H, s), 3.17 (1H, dd, J=10.4, 8.0 Hz), 2.17 (1H, m), 2.04 (1H, m), 1.92 (1H, m), 1.81 (1H, m), 1.68 (2H, m), 1.06 (3H, s), 0.72 (3H, s).

Provenance & Evidence