Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Formula: C7H10O2
Lithium bis(trimethylsilyl)amide (4.95 mL, 4.95 mmol, 1.0 M in THF, 1.55 equiv.) was cooled to -78 C, then i-butyl propiolate (604 mg, 4.789 mmol, 1.5 equiv.) in 3 mL THF was added and the reaction mixture was stirred for 45 min. The solution was then added via cannula over 10 min to ketone (3R)-9 (953 mg, 3.193 mmol, 1 equiv.) in 5 mL THF at -78 C and stirred for 2 h. The reaction was quenched with satd aq NH4Cl (50 mL), warmed to rt, and extracted with EtOAc (4 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (50%? 100% CH2Cl2 in hexanes) yielded the ester (15,3R)-10 as a clear viscous oil (1.05 g, 78%). IR (ATR): 3400, 2956, 2932, 2888, 2860, 2248, 1710, 1473, 1395, 1371, 1258, 1204, 1153, 1114, 1039, 1013, 909, 888, 838, 781, 751, 732, 695, 672, 657. 1H-NMR (500 MHz; CDCl3): delta 7.63-7.60 (m, 1H), 7.47-7.45 (m, 2H), 7.38-7.37 (m, 1H), 5.19 (dd, 7 = 8.0, 6.3 Hz, 1H), 2.96 (d, 7 = 2.3 Hz, 1H), 1.49 (s, 9H), 0.95 (s, 9H), 0.24 (s, 6H). 13C-NMR (126 MHz; CDCl3): delta 151.8, 139.5, 139.1, 130.9, 130.3, 124.9, 124.4, 124.2, 84.2, 80.6, 78.2, 74.9, 74.4, 28.0, 25.7, 18.2, -4.65, -4.84. 19F-NMR (471 MHz; CDCl3): delta delta -115.05 (d, 7 = 224.7 Hz, 1F), -128.46 (d, 7 = 224.6 Hz, 1F). HRMS (ESI) m/z calcd for C22H30O4F2SiNa ([M+Na]+) 441.1779; found 441.1785.
The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; TAN, Derek, Shieh; EVANS, Christopher, E.; SHARMA, Indrajeet; TONGE, Peter, James; MATARLO, Joe, S.; (242 pag.)WO2017/59411; (2017); A1;,
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