Electric Literature of 2062-98-8, These common heterocyclic compound, 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, its 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.
Example 11 A mixture of ethanolamine (13 g, 28 mmole) and ether (30 mL) was cooled to 15 C. Perfluoro-2-methyl-3-oxahexanoyl fluoride (33 g in ether 50 mL) was added dropwise to keep the reaction temperature below 25 C. After the addition, the reaction mixture was stirred at room temperature for one hour. The solid was removed by filtration and the filtrate was washed with hydrochloric acid (0.5N, 30 mL), water (2 times 30 mL), sodium hydrogen carbonate solution (0.5N, 20 mL), water (30 mL), and sodium chloride solution (saturated, 20 mL). It was then concentrated and dried in vacuum over night at room temperature to give a white solid 35 g, yield 95%. H NMR (CDCl3) 1.67 (br s, 1H), 3.57 (m, 2H), 3.80 (t, J=5 Hz, 2H), 6.91 (br s, 1H) ppm. F NMR (CDCl3) -81.2 (dm, J=148 Hz, 1F), -81.7 (t, J=7 Hz, 3F), -82.7 (d, J=3 Hz, 3F), -85.2 (dm, J=148 Hz, 1F), -130.1 (s, 2F), -133.2 (m, 1F) ppm. The product is N-(perfluoro-2-methyl-3-oxahexanoyl)-2-aminoethanol. A 250-mL flask was charged with triethylamine (8.2 g), THF (80 mL), and N-(perfluoro-2-methyl-3-oxo-hexanoyl)-2-aminoethanol (25 g). Methacryloyl chloride (8.44 g in tetrahydrofuran, 20 mL) was added dropwise to the above mixture at 5 C. The mixture was stirred at room temperature overnight. The reaction mixture was poured into water (200 mL) and two layers were formed. The aqueous layer (top layer) was extracted with methylene chloride (five time 50 mL). The combined methylene chloride extracts and original organic layer were washed with water (six times 60 mL), neutralized with dilute hydrochloric acid (0.5N), dried over anhydrous sodium sulfate, concentrated and dried on vacuum to give a oil, N-(perfluoro-2-methyl-3-oxahexanoyl)-2-aminoethyl methacrylate (27.06 g), yield 92%. H NMR (CDCl3) 1.94 (m, 3H), 3.72 (m, 2H), 4.33 (m, 2H), 5.63 (m, 1H), 6.12 (m, 1H), 6.88 (br s, 1H) ppm. F NMR (CDCl3) -81.2 (dm, J=148 Hz, 1F), -81.7 (t, J=7 Hz, 3F), -82.7 (d, J=3 Hz, 3F), -85.2 (dm, J=148 Hz, 1F), -130.1 (s, 2F), -133.4 (m, 1F) ppm.
Statistics shows that Perfluoro(2-methyl-3-oxahexanoyl) fluoride is playing an increasingly important role. we look forward to future research findings about 2062-98-8.