Some common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, molecular formula is C7H12O3, 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. Application In Synthesis of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate
In a three-necked flask fitted with thermometer, dropping funnel and gas exhaust, 7.39 g (58.19 mmol) of oxalyl chloride were initially charged in 116 ml of abs. dichloromethane at -78 C. 9.08 g (116.38 mmol) of dimethyl sulphoxide, dissolved in 8 ml of abs. dichloromethane, were then slowly added dropwise (careful: intensive evolution of gas), with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 5 min 7.63 g (52.90 mmol) of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (described in M. H. Parker et al. U.S. Pat. Appl. Publ., 20120053146), dissolved in 196 ml of abs. dichloromethane, were then slowly added dropwise, with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 10 min 26.72 g (264.51 mmol) of triethylamine were then slowly added dropwise, with the internal temperature being kept between -70 C. and -78 C. The reaction mixture was stirred at -78 C. for another 10 min and then warmed to RT over 2 h. The mixture was diluted with 700 ml of methyl tert-butyl ether, the precipitate was filtered off and the filtrate was concentrated at 30 C. and 100 mbar. The residue was purified by flash chromatography (mobile phase: dichloromethane). This gave 7.30 g (97% of theory, purity about 95% according to NMR) of the title compound. (0307) 1H NMR (500 MHz, CDCl3): delta [ppm]=1.32 (t, 3H), 1.58-1.63 (m, 2H), 1.65-1.70 (m, 2H), 4.28 (q, 2H), 10.41 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3697-68-5, its application will become more common.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (46 pag.)US2016/145271; (2016); A1;,
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