Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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. category: chlorides-buliding-blocks
General procedure: To a solution of 4-phenylbutyl benzoate 1a (127 mg, 0.5 mmol) and N-hydroxyphthalimide (8.16 mg, 0.05 mmol) in CH3CN (1.7 mL) was added cerium(IV) ammonium nitrate (548 mg, 1.0 mmol) at 0 C. The reaction mixture was immediately warmed to room temperature and stirred for 2 h. The mixture was then filtered through a short column of alumina (hexane-EtOAc 1:1), and the filtrate was concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 70:1 to 50:1) to provide 4-benzoyloxy-1-phenylbutyl nitrate 2a in 81% yield (128 mg). 1.0 mmol) at 0 C. The reaction mixture was immediately warmed to room temperature and stirred for 2 h. The mixture was then filtered through a short column of alumina (hexane-EtOAc 1:1), and the filtrate was concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 70:1 to 50:1) to provide 4-benzoyloxy-1-phenylbutyl nitrate 2a in 81% yield (128 mg).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-52-9, its application will become more common.
Reference:
Article; Kamijo, Shin; Amaoka, Yuuki; Inoue, Masayuki; Tetrahedron Letters; vol. 52; 36; (2011); p. 4654 – 4657;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics