Synthetic Route of 2687-12-9, These common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, 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.
A flame dried 100 mL round-bottomed flask under Ar was charged with chlorotrioctylstannane (2.0 g mL, 4.05 mmol), cinnamyl chloride (0.8 g, 5.3 mmol),magnesium powder (0.14 g, 5.7 mmol), a crystal of iodine and dry THF (50 mL). The resulting mixture was sonicated at 50 C for 6 h and was then stirred overnight at room temperature. Water (50 mL) was added and the mixture was transferred to a separating funnel. The water layer was separated and the remaining organic layer was diluted with heptane (100 mL), washed with acetonitrile (2 x 50 mL), water (50 mL) and finally againwith acetonitrile (3 x 50 mL). Drying on MgSO4, filtration and concentration in vacuo afforded a crude product, which was purified by column chromatography on silica gel using petroleum ether as the eluent, providing trioctyl(3-phenylallyl)stannane (1.42 g, 2.5 mmol, 62 %) as a faint yellow oil. ?H-NMR (CDC13, 400 MHz) & 7.40-7.26 (m, 2H), 7.25-7.20 (m, 2H), 7.12-7.06 (m, 1H),6.39 (dt, 1H, I = 15.5, 8.8 Hz), 6.17 (dt, 1H, I = 15.5, 1.0 Hz), 2.04-1.84 (m, 2H), 1.68-1.40 (m, 6H), 1.36-1.16 (m, 30H), 0.98-0.82 (m, 15 H); ?3C-NMR (100 MHz, CDC13):138.9, 131.3, 128.5, 125.8, 125.3, 125.1, 34.5, 32.0, 29.4, 29.3, 27.0, 22.8, 16.3, 14.2, 10.0;?9Sn-NMR (149.2 MHz, CDC13) & -12.8.
The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; UNIVERSITEIT ANTWERPEN; KUVSHINOV, Alexandr; FRANCK, Philippe; DEPRAETERE, Stefaan; MAES, Bert; DE HOUWER, Johan; WYBON, Clarence; STERCKX, Hans; SERGUEEV, Serguei; WO2013/167585; (2013); A2;,
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