Reference of 928-50-7,Some common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, molecular formula is C5H9Cl, 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.
General procedure: Sodium azide (0.5 g, 8 mmol) was added to the stirredsolution of chlorides 1b,e,f or tosylates 1c,d (6 mmol) indry DMSO (8 ml) at room temperature. The reactionmixture was stirred at 70C for 15 h, then washed well withwater (3×10 ml) and extracted with CH2Cl2 (2×10 ml). Combined organic layers were dried over MgSO4, filtered,and concentrated to obtain the crude azides 2b-f. Resultingazides were dissolved in Et2O (10 ml), PPh3 (1.6 g, 6 mmol)was added, the reaction mixture was stirred at 0C for 1.5 h.Then water (1 ml) was added and the reaction mixture wasstirred at room temperature overnight. After the completion,the reaction mixture was poured onto crushed ice andextracted with CH2Cl2 (3×10 ml). Organic layers werecombined and dried over MgSO4, filtered, and concentratedunder reduced pressure to obtain amines 3b-f. Solution ofamine 3a-f in CH2Cl2 (10 ml) was stirred with K2CO3(2.2 g, 16 mmol) at 0C for 15 min. Acryloyl chloride(0.6 ml, 7 mmol) was added dropwise at 0C, and themixture was stirred at room temperature for 6 h. Thereaction was monitored by TLC. After completion of thereaction, cold water (10 ml) was added and the mixture wasextracted with CH2Cl2 (3×10 ml). The combined organiclayers were washed with brine, dried over anhydrous MgSO4,filtered, and concentrated under reduced pressure. Thecrude diene amides 4a-f were purified on silica gel column,eluting with EtOAc-petroleum ether with increasing gradient.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloropent-1-ene, its application will become more common.
Reference:
Article; Gondal, Humaira Yasmeen; Buisson, Didier; Chemistry of Heterocyclic Compounds; vol. 52; 3; (2016); p. 183 – 191; Khim. Geterotsikl. Soedin.; vol. 52; 3; (2016); p. 183 – 191,9;,
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