The origin of a common compound about 14719-21-2

The synthetic route of 14719-21-2 has been constantly updated, and we look forward to future research findings.

Related Products of 14719-21-2,Some common heterocyclic compound, 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, molecular formula is C5H4F3NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solution of 6 (1.37 g; 2.45 mmol) in anhydrous DMF (11 mL) were added tetrakis (triphenylphosphine) palladium (0)(286 mg; 0.245 mmol) and CuI (101 mg; 0.532 mmol). The solution was stirred at room temperature for 10 min. Then N-propargyltrifluoroacetamide (1.12 g; 7.43 mmol) and triethylamine (0.68 mL; 4.90 mmol) were added. The reaction was stirred at room temperature for 13 h with exclusion of air and light. Most DMF was removed under vacuum and the residue was dissolved in ethyl acetate (100 mL) . The solution was washed by saturated aqueous NaHCO3 and NaCl respectively, and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using ethyl acetate-hexane (1:3-1.5) and CH3OH- CH2Cl2 (1:30) respectively as the eluent to afford 7 as yellow solid (1.34 g; 94% yield): 1H NMR (400 MHz, CD3OD) delta 7.34 (s, IH, 6-H) , 6.42 (dd, J = 6.2, 7.7 Hz, IH, l’-H), 5.88-5.99 (m, IH, CH2CJf=CH2), 5.28-5.35 (dm, J = 17.3 Hz, IH, one of CH2CH=CJf2), 5.16-5.21 (dm, J = 10.5 Hz, IH, one of CH2CH=CJf2), 4.29 (s, 2H, C?CCJf2) , 4.24 (m, IH, 3′-H), 4.00-4.09 (m, 3H, 4′-H and CJf2CH=CH2), 3.98 (s, 3H, 4-OCJf3), 3.76-3.84 (m, 2H, 5′- H), 2.32-2.45 (m, 2H, 2′-H), 0.94 (s, 9H, C (CH3) 3)/ 0.12 (s, 3H, one of SiCJf3), 0.11 (s, 3H, one of SiCJf3); 13C NMR (100 MHz, CD3OD) 5 165.0, 161.2, 158.1 (q, J = 36 Hz, COCF3), 154.2, 135.6, 125.0, 117.2 (q, J = 284 Hz, COCF3), 117.0, 99.2, 97.3, 86.0, 84.6, 84.5, 80.3, 78.0, 71.0, 64.8, 53.8, 39.0, 30.9, 26.5, 19.3, -5.1, – 5.2; HRMS (FAB+) calculated for C26H37O5N5F3Si (M+H+) : 584.2516, found: 584.2491.

The synthetic route of 14719-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; WO2007/53702; (2007); A2;,
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