Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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. COA of Formula: C4H6Cl2
To a solution of 0.235 g of (+)-(1-Benzyloxycarbamoyl-but-3-enyl)-carbamic acid tert-butyl ester (9a) in 8 mL of tetrahydrofuran was added 0.635 g of cesium carbonate. The reaction was heated to 60oC for 60 minutes, and then 1 mL of 2-chloro-3-methallyl chloride was added. The reaction was heated for an additional 20 hours. The reaction was then cooled, quenched with NH4Cl(aq.) solution, and extracted with ethyl acetate. The organic layers were washed with NH4Cl(aq.) and NaCl(aq.) solutions. The aqueous layers were re-extratced with ethyl acetate, and the organic layers combined and dried over Na2SO4(s). Filtration and solvent removal gave a white, oily solid. Column chromatography (hexanes/ethyl acetate gadiant) on silica gel, followed by fraction combination, and solvent removal gave 170 mg of a white solid (57% yield). 1H NMR (CDCl3): d 2.36 (quint, 1H, J=7 Hz), 2.48 (quint, 1H, J=7 Hz), 4.06 (d, 2H, J=4 Hz), 4.12 (m, 1H), 4.68 (m, 1H), 4.88 (bs, 1H), 4.99 (m, 2H), 5.13 (m, 1H), 5.26 (m, 2H), 5.72 (m, 1H), 7.4 (m, 5H); MS: 839 (2M+Na), 431 (M+Na).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1871-57-4, its application will become more common.
Reference:
Article; Wilson, Lawrence J.; Wang, Bingbing; Yang, Shyh-Ming; Scannevin, Robert H.; Burke, Sharon L.; Karnachi, Prabha; Rhodes, Kenneth J.; Murray, William V.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 21; (2011); p. 6485 – 6490;,
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