Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl fluoromalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 685-88-1, COA of Formula: C7H11FO4
Diethyl 2-fluoromalonate (5 g, 28.1 mmol) was added, over 10 min, to a stirred suspension of sodium hydride (1.347 g, 33.7 mmol) in tetrahydrofuran (50 mL) at 0C and the resulting colourless solution was stirred at 0 C for 15 min. and then at RT for 30 min. The solution was cooled to 0 C, a solution of 6-bromohex-l-ene (4.58 g, 28.1 mmol) in THF (20 mL) was then added over 5 min. and the resulting reaction mixture was heated to 60 C and stirred for 16 h. Then the reaction mixture was cooled to 0 C, quenched with ice cold water (100 mL) and extracted with ethyl acetate (2 x 200 mL). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over anhydrous sodium sulphate, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by combiflash chromatography (80 g Redisep S1O2 column, eluting with 10 % EtOAc in n- hexanes) to afford the title compound 162A (5 g, 68%) as a colourless oil. LC-MS retention time = 3.30 min; m/z = 261.2 [M+H]+ KINETIX XB-C18, (75 X 3) mm, 2.6 micron column; Flow rate: 1 mL/min; Mobile Phase A: 10 mM HCO2NH4 in 98% Water/ 2% ACN; Mobile Phase B: 10 mM HCO2NH4 in 2% Water/ 98% ACN; 20% B to 100% B over 4.6 min, then hold 0.4 min. at 20% B with flow rate 1.5 mL/min; Detection: UV at 220 nm. NMR (400MHz, CDCh) delta ppm 5.78 (ddt, J=17.1 , 10.3, 6.6 Hz, 1H), 5.01 (d, J=17.2 Hz, 1H), 4.95 (d, J=6.4 Hz, 1H), 4.34 (q, J=5.6 Hz, 4H), 2.18 – 2.05 (m, 4H), 1.43 – 1.40 (m, 4H), 1.30 (t, J=7.2 Hz, 6H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diethyl fluoromalonate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (2018); A1;,
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