Electric Literature of 4277-34-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4277-34-3 as follows.
(E)-2-Cyanoethyl cyclooct-4-enyl diisopropylphosphoramidite (2). To a solution of (E)-Cyclooct-4-enol (70 mg, 0.56 mmol) in 2 ml of absolute CH2Cl2 under argon diisopropylethylamine (0.33 ml, 1.90 mmol) was added. The mixture was cooled to 0C and 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite (141 mul, 0.63 mmol, 1.05 eq) was added. After stirring for one hour at RT, the reaction mixture was directly loaded on a silica column. Purification by flash chromatography (hexane/ethyl acetate 95:5) yielded the product as colourless oil (100 mg, 0.31 mmol, 55%). 1H-NMR (500 MHz, CDCl3, 25C, TMS): delta = 1.16-1.19 (m, 12H), 1.55-1.63 (m, 2H), 1.86-2.37 (m, 8H), 2.63 (t, J = 6.55 Hz, 2H), 3.51-3.61 (m, 3H), 3.72-3.85 (m, 2H), 5.38-5.44 (m, 1 H), 5.54-5.61 (m, 1H). 13C {1H, 31P} NMR (75 MHz, CDCl3, 25C, TMS): delta=20.3, 24.4, 24.6, 31.1, 31.3, 32.7, 32.8, 34.4, 40.0, 40.3, 42.9, 43.0, 43.2, 58.1, 58.3, 79.6, 80.0, 117.6, 132.6, 135.1, 135.2. 31P-NMR (121 MHz, CDCl3,25C, H3PO4): delta=145.5, 146.0.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4277-34-3, its application will become more common.
Reference:
Patent; Deutsches Krebsforschungszentrum; Ruprecht-Karls-Universitaet Heidelberg; Schoch, Juliane; Jaeschke Andres; Samanta, Ayan; Wiessler, Manfred; EP2565199; (2013); A1;,
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