6314-28-9, Benzo[b]thiophene-2-carboxylic acid is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Following the typical procedure for 3a using 2b (178 mg, 1 mmol) and 3-(1-hydroxycyclohexyl)prop-2-ynenitrile (1c, 179 mg, 1.2 mmol) in MeCN (5 mL), and Et3N (101 mg, 1 mmol) with microwave irradiation at 100 C for 6.5 h (or was stirred at 20-25 C for 23 d, or at 40-45 C for 3 d). The residue was concentrated to give solid matter (308 mg) containing the furan-3(2H)-one 3f and traces of carboxylic acid 2b (1H NMR). The mixture was dissolved in Et2O (40 mL) and washed with ~0.2% NaHCO3 solution (7 ¡Á 1 mL), then it was washed with small amount of H2O (neutral reaction on litmus paper). The organic solution was dried (MgSO4) and concentrated to give 3f as pale yellow crystals; yield: 254 mg (82 %), or 31 mg (10 %, at 20-25 C), or 52 mg (17 %, at 40-45 C); mp 187-188 C. IR (KBr): 3079, 3058 (C=CH), 2937, 2860 (CH), 2220 (CN), 1704(C), 1566, 1516 (C=C), 1459, 1446, 1433, 1383, 1366, 1326,1314, 1279, 1265, 1214, 1197, 1163, 1149, 1121, 1115, 1068, 1031,985, 970, 950, 932, 909, 900, 868, 854, 845, 823, 774, 756, 723,681, 672, 655, 548, 539, 497, 468, 428 cm-1. 1H NMR (400.1 MHz, CDCl3): delta = 1.41 (m, 1 H, H8), 1.65-1.90 (m,9 H, H6, H7, H8, H9, H10), 7.47 (m, 1 H, H6?), 7.53 (m, 1 H, H5?), 7.91 (d, J = 8.0 Hz, 1 H, H7?), 7.96 (d, J = 8.0 Hz, 1 H, H4?), 8.53 (s, 1 H, H3?). 13C NMR (100.6 MHz, CDCl3): delta = 21.4, 24.1, 31.8 (C6, C7, C8,C9, C10), 87.5 (C5), 93.8 (C3), 112.3 (CN), 122.6 (C7?), 125.8(C6?), 126.3 (C5?), 128.6 (C4?), 129.1 (C2?), 132.5 (C3?), 138.6 (C3a), 142.6 (C7a), 180.7 (C2), 198.5 (C4). MS (EI): m/z (%) = 310 (20) [M]+1, 309 (78) [M]+, 268 (22), 267(32), 255 (16), 254 (100), 241 (11), 184 (15), 183 (79), 161 (43), 139 (23), 133 (20), 89 (11). Anal. Calcd for C18H15NO2S (309.38): C, 69.88; H, 4.89; N, 4.53;S, 10.36. Found: C, 69.41; H, 4.83; N, 4.53; S, 10.82., 6314-28-9
The synthetic route of 6314-28-9 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Mal’Kina, Anastasiya G.; Volostnykh, Olga G.; Stepanov, Anton V.; Ushakov, Igor A.; Petrushenko, Konstantin B.; Trofimov, Boris A.; Synthesis; vol. 45; 24; (2013); p. 3435 – 3441;,
Benzothiophene – Wikipedia
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