344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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 dimethyl fluoromalonate (1 mmol, 150.11 mg) in anhydrous methanol (10 ml) was added a solution of n-octylamine (1 mmol, 166 mul) in methanol (5 ml) drop wise over the period of one hour at room temperature. It was then further stirred at room temperature for two hours. The solution was rotary evaporated and the residue redissolved in ethyl acetate. The ethyl acetate solution was sequentially washed with 2 M HCI (2×10 ml) and saturated sodium chloride (1×15 ml) solution. Drying over MgSO4 and rotary evaporation of organic solvent gave white solid that was a mixture of bisamide and ethyl 4-aza-2-fluoro-3-oxododecanoate. Desired product was purified as a white solid by PLC in 40-60 petroleum ether – diethyl ether (3:2), (117 mg, 47%).TLC Rf 0.23, petroleum ether- diethyl ether (3:2)1H NMR (400 MHz, CDCI3) delta 0.88 (3H, t, J 6.4 Hz, (CH3(CH2)/), 1.29 (10H, m, CH3(CH2)5), 1.54 (2H, br s, CH3(CH2)5CH2), 3.32 (2H, m, J 6.6 Hz, CH3(CH2)6CH2), 3.9 (3H, s, OCH3), 5.28 (1 H, d, J 49.2, C(H)F), 6.42 (1 H, s, NH).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-fluoromalonate, its application will become more common.
Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; WO2007/135466; (2007); A2;,
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