As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1628-89-3, name is 2-Methoxypyridine, molecular formula is C6H7NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Formula: C6H7NO
A flame-dried, 20 ml argon-filled Schlenk-tube was charged with 2-methoxypyridine (15) (55 mg, 0.50 mmol, 1 .0 equiv.), and dry MeCN (2.0 ml, c = 0.25 M). Trifluoroacetic anhydride (0.21 ml, 0.32 g, 1.5 mmol, 3.0 equiv.) was added while stirring the reaction mixture. After cooling to 0 C, tetrafluorothianthrene reagent (97 % (w/w) tetrafluorothianthrene-S-oxide 1 , 3 % (w/w) tetrafluorothianthrene 2, 157 mg, 0.50 mmol, 1 .0 equiv.) was added in one portion, followed by the addition of trimethylsilyl-trifluormethanesulfonate (181 pi, 0.22 g, 1.0 mmol, 2.0 equiv.) in one portion at 0 C, leading to a dark suspension. The vial was sealed and the mixture was stirred at 0 C for 1 h, followed by stirring at 25 C for 1 h. The reaction mixture was concentrated under reduced pressure, and diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2 x ca. 10 ml, 5 % w/w), and with water (2 x ca. 10 ml). The DCM layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / /-PrOH, (30:1 (v/v)). The product was dissolved in 5 ml DCM, and precipitated with 20 ml Et20. The precipitate was dried in vacuo to afford 21 1 mg (87 %) of 15a as colorless solid.NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 8.35 (dd, J = 9.1 Hz, 7.2 Hz, 2H), 8.06 (dd, J = 2.9 Hz, 0.5 Hz, 1 H), 7.97 (dd, J = 9.9 Hz, 7.1 Hz, 2H), 7.54 (dd, J = 9.2 Hz, 2.9 Hz, 1 H), 6.91 (dd, J = 9.2, 0.6 Hz, 1 H), 3.93 (s, 3H).13C {1H} NMR (128 MHz, CD3CN, 298 K, d): 168.1 , 154.8 (dd, J = 261.6 Hz, 13.1 Hz), 151 .7 (dd, J = 155.6 Hz, 13.7 Hz), 149.5, 139.6, 134.9 (dd, J = 8.8 Hz, 4.0 Hz), 125.0 (dd, J = 22.3 Hz, 2.4 Hz), 121.3 (d, J = 21 .9 Hz), 1 15.5 (dd, J = 7.2 Hz, 3.6 Hz), 1 14.2, 1 12.1 , 55.5. 19F {1H} NMR (471 MHz, CD3CN, 298 K, d): -125.6 (d, J = 20.4 Hz), -133.6 (d, J = 20.4 Hz), -151 .1 (bs), -151.1 (bs).HRMS-ESI(m/z) calc?d for CI8H10F4NOS2+[M-BF4]+, 396.013700; found, 396.013448; deviation: 0.6 ppm.
With the rapid development of chemical substances, we look forward to future research findings about 1628-89-3.
Reference:
Patent; STUDIENGESELLSCHAFT KOHLE MBH; RITTER, Tobias; BERGER, Florian; (146 pag.)WO2020/94673; (2020); A1;,
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