Synthetic Route of 6318-51-0, Adding some certain compound to certain chemical reactions, such as: 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone,molecular formula is C12H8ClNO, 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 6318-51-0.
Under argon atmosphere, cinchonine (440 mg, 1.0 mmol) was suspended in tetrahydrofuran (absolute, 2.0 mL), and to this suspension was added a Reformatsky reagent (0.5 M; 8.0 mL, 4.0 mmol) dropwise under ice-cooling. After stirring for 10 minutes, pyridine (0.30 mL, 2 mmol) was added thereto dropwise. After stirring for 20 minutes under ice-cooling, the mixture was cooled to -40C. A solution of 2- (4-chlorobenzoyl) pyridine (218 mg, 1. 0 mmol) in tetrahydrofuran (absolute, 4.0 mL) was added dropwise over 10 minutes, and the mixture was stirred at -40 C for 4 hours. To this reaction solution was added 1N HCl (20 mL) , which was then extracted with ethyl acetate (20 mL×2). The extracted solution was washed successively with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution. After the organic layer was dried with sodium sulfate, the solvent was removed under reduced pressure. The residue was analyzed with high performance liquid chromatography. Consequently, the yield was 81% and the enantiomer excess was 91%.1H NMR (400 MHz, CDCl3) delta: 1.33 (9H, s), 3.08 (1H, d, J = 16.0 Hz), 3.49 (1H, d, J = 16.0 Hz), 5.52 (1H, s), 7.1-7.7 (7H, m), 8.4-8.6 (1H, m). IR (KBr) nucm-1: 3358, 2977, 1694, 1591, 1490, 1467, 1368, 1159, 1090, 1013, 830, 785, 755, 591. High Performance Liquid Chromatography Column: CHIRALCEL OJ Mobile phase: Hexane/Ethanol/Trifluoroacetic acid (99/1/0.1) Flow rate: 0.5 mL/min. Detection: UV (254 nm) Temperature: Room Temperature Retention Time: 24.5 minutes (enantiomer 17.3 minutes)
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Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1489070; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem