ABSTRACT
Product (12). Compound 10 (117 mg, 0.8 mmol) was added to 2 equivalents of dimethyl malonate (11) (211 mg, 1.6 mmol, 183 μl) and mixed. Two equivalents of piperidine (1.6 mmol, 136 mg, 158 μl) was added to the mixture and stirred at room temperature for 10 min. 5.0 mg (0.04 mmol) of catalyst 1 was added. The reaction mixture was stirred to the completion and diluted with ethyl acetate (10 mL). It was washed twice with water. (2 × 5 mL). The organic layer (product 12) was dried over anhydrous Na2SO4 (2 g). According to the type of catalysts (1-6), 186-222 mg (84% to 100%) of product 12 was isolated (see Table 13.2). The reaction was repeated with the same mole ratio using catalysts 2-6. 1H NMR (400 MHz, 298 K, ppm, in CDCl3): δ = 7.22-7.09 (m, 5H, H-arom), 3.89 (ddd, J = 5.6 Hz, J = 8.4 Hz, J = 9.6 Hz, 1H, CH2-CH), 3.65 (s, 3H, O-CH3), 3.63 (s, 3H, O-CH3), 3.48 (m, 1H, CO-CH-CO), 3.29 (m, 1H, CO-CHH), 2.87 (dd, J = 5.3 Hz, J = 6.9 Hz, 1H, CO-CHH), 1.94 (s, 3H, CO-CH3). 13C NMR (101 MHz, 298 K, ppm, in CDCl3): δ = 205.58 (C = O), 168.24 (C = O), 167.96 (C = O), 167.72 (C-arom), 163.75 (C-arom), 140.10 (C-arom), 128.22 (C-arom), 127.68 (C-arom), 126.95 (C-arom), 56.80 (O-CH3), 52.04 (O-CH3), 46.81(CO-CH-CO), 40.13(CO-CH2), 29.99 (CH-CH2), 24.04 (CO-CH3).
