反应详情

3-Trifluoromethylsulphonyloxy-2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy benzaldehyde (46) (0.844 g., 1.79 mmol) is coupled with phenyltributylstannane (0.760 g., 2.06 mmol) via the method of Example 3 to afford 2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy-[1,1'-biphenyl]-3-carboxaldehyde (47) (0.380 g., 0.96 mmol, 54%): chromatographed on silica gel using CH2Cl2 /hexane to afford an oil; 1H NMR (300 MHz, CDCl3) 10.32 (s, 1H, CHO), 7.81 (dd, J=2, 8 Hz, 1H, ArH), 7.61 (m, 3H, ArH), 7.44 (m, 3H, ArH), 7.28 (dd, J=8, 8 Hz, 1H, ArH), 7.20 (d, J=8 Hz, 1H, ArH), 6.88 (d, J=2 Hz, 1H, ArH), 6.84 (dd, J=2, 8 Hz, 1H, ArH), 4.46 (s, 2H, ArCH2O), 1.67 (s, 4H, CH2CH2), 1.22 (s, 6H, 2×CH3), 1.17 (s, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 190.30 (C=0), 159.90, 145.01, 137.32, 137.23, 136.56, 132.38, 130.29, 129.23, 128.62, 127.86, 127.31, 127.18, 126.83, 126.18, 124.62, 34.96, 34.93, 34.15, 31.78, 31.75; IR (film) 2958, 2926, 1688, 1584, 1458, 1364, 1244, 1210, 764, 700 cm-1 ; MS (DCI) m/e 398 (MH+), 201 (C15H21+).