Reaction Steps
As starting materials for the coupling reaction menadione and 4-(trifluoromethoxy)phenylacetic acid were used. Synthesis is realized according to the general procedure described in general procedure of example 1. After chromatography on silica gel (petroleum ether:CH2Cl2=1:1, UV), 494 mg (1.43 mmol, 78% yield) of P_TM97 were isolated as yellow solid. Melting point: 64-65° C. —1H-NMR (300 MHz, CDCl3): δ=8.03-8.10 (m, 2H), 7.65-7.71 (m, 2H), 7.34 (d, 3J=8.74 Hz, 2H), 7.09 (d, 3J=8.08 Hz, 2H), 4.01 (s, 2H), 2.23 (s, 3H). —13C-NMR (75 MHz, CDCl3): δ=185.17 (Cq), 184.52 (Cq), 147.42 (Cq), 144.72 (Cq), 144.57 (Cq), 136.76 (Cq), 133.57 (CH), 132.07 (Cq), 131.92 (Cq), 129.87 (CH), 126.47 (CH), 126.33 (CH), 121.15 (CH), 120.44 (q, 1JCF=256.91 Hz), 31.78 (CH2), 13.27 (CH3). —EI MS (70 eV, m/z (%)): 346.0 ([M]+, 32), 331.1 (100), 261.1 (8), 175.1 (71), 76.0 (10), 28.0 (49). —IR (KBr): 3077 cm−1 (w), 3047 (w), 3021 (w), 3003 (w), 2963 (w), 2948 (w), 2853 (w), 2143 (w), 2004 (w), 1975 (w), 1901 (w), 1876 (w), 1664 (vs), 1620 (m), 1596 (s), 1508 (s), 1446 (w), 1435 (w), 1378 (m), 1333 (s), 1297 (vs), 1271 (vs), 1217 (vs), 1188 (vs), 1166 (vs), 1111 (m), 1019 (w), 976 (m), 793 (w), 770 (w), 708 (s), 692 (w). —EA: obs. C, 65.78%; H, 3.98%, calcd. C, 65.90%; H, 3.78% for C19H13F3O3.
