Reaction Steps
A 25-mL flask was charged with 6 (21 mg, 0.03 mmol), 20% Pd(OH)2 on carbon (nominally 50% in water, 7 mg), and 1 mL each of EtOAc and MeOH. The suspension was stirred under a hydrogen balloon at room temperature for 5-17 hours. The catalyst was filtered off (Celite), the residue concentrated to give 20 mg (quantitative) of a pale yellow foam, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.30-7.15 (m, 13H), 6.95 (s, 1H), 6.90 (m, 2H), 5.45 (ABq, J=16.4 Hz, 2H), 4.21 (td, J=8.5, 2.1 Hz, 1H), 4.09 (q, J=7.0H, 2H), 3.75 (d, J=8.6 Hz, 1H), 2.72-2.58 (m, 4H), 2.46 (t, J=7.4 Hz, 2H), 1.06-1.51 (m, 2H), 1.48-1.44 (m, 2H), and 1.22 (t, J=7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 173.45, 165.67, 142.18, 141.36, 139.65, 138.95, 129.11, 128.99, 128.88, 128.72, 128.30, 127.20, 127.15, 126.94, 126.01, 120.86, 120.09, 119.67, 73.09, 60.66, 58.67, 48.23, 35.37, 34.81, 21.23, 20.70, and 14.50; IR (KBr) 3428, 3027, 2933, 1732, 1663, and 1450 cm−1; LRMS-El m/z 481 ([M−CO2+], 64%), 167 ([Ph2CH3+], 75%), and 91 ([PhCH2+], 100%).
