The synthetic route of 89359-54-6 has been constantly updated, and we look forward to future research findings.
Application of 89359-54-6, These common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, 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.
To a flame dried 500 mL RB flask, freshly activated Mg turnings (9 g) were added and the flask was equipped with a magnetic stir bar, an addition funnel and a reflux condenser. This set-up was degassed and flushed with argon and 100 mL of anhydrous ether was added to the flask via syringe. The bromide 3 (51.3 g, 250 mmol) was dissolved in anhydrous ether (100 mL) and added to the addition funnel. About 5 mL of this ether solution was added to the Mg turnings while stirring vigorously. An exothermic reaction was noticed (to confirm/accelerate the Grignard reagent formation, 5 mg of iodine was added and immediate decolorization was observed confirming the formation of the Grignard reagent) and the ether started refluxing. The rest of the solution of the bromide was added dropwise while keeping the reaction under gentle reflux by cooling the flask in water. After the completion of the addition the reaction mixture was kept at 35 C for 1 hour and then cooled in ice bath. Ethyl formate (9 g, 121 mmol) was dissolved in anhydrous ether (100 mL) and transferred to the addition funnel and added dropwiseto the reaction mixture with stirring. An exothermic reaction was observed and the reaction mixture started refluxing. After the initiation of the reaction the rest of the ethereal solution of formate was quickly added as a stream and the reaction mixture was stirred for a further period of 1 h at ambient temperature. The reaction was quenched by adding 10 mL of acetone dropwise followed by ice cold water (60 mL). The reaction mixture was treated with aq. H2S04 (10 % by volume, 300 mL) until the solution became homogeneous and the layers were separated. The aq. phase was extracted with ether (2×200 mL). The combined ether layers were dried (Na2S04) and concentrated to afford the crude product which was purified by column (silica gel, 0-10% ether in hexanes) chromatography. The product fractions were evaporated to provide the pure product 249 as a white solid (30.6 g, 90%). 1H NMR (400 MHz, CDC13) delta 7.26 (s, 1H), 5.81 (ddt, J = 16.9, 10.2, 6.7 Hz, 8H), 5.04 – 4.88 (m, 16H), 3.57 (dd, J = 7.6, 3.3 Hz, 4H), 2.04 (q, J = 6.9 Hz, 16H), 1.59 (s, 1H), 1.45 (d, J = 7.5 Hz, 8H), 1.43 – 1.12 (m, 94H), 0.88 (t, J = 6.8 Hz, 2H). 13C NMR (101 MHz, cdcl3) delta 139.40, 114.33, 77.54, 77.22, 76.90, 72.21, 37.70, 34.00, 29.86, 29.67, 29.29, 29.12, 25.85.
The synthetic route of 89359-54-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ALNYLAM PHARMACEUTICALS, INC.; MAIER, Martin; JAYARAMAN, Muthusamy; AKINC, Akin; MATSUDA, Shigeo; KADASAMY, Pachamuthu; RAJEEV, Kallanthottathil, G.; MANOHARAN, Muthiah; WO2013/86354; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary