Application of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.
Example 193A(+/-)-tert-Butyl 1-[(3-bromo-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate; 42.2 ml (105.5 mmol) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution, cooled to from -20 C. to -30 C., of 14.8 ml (105.5 mmol) of diisopropylamine in 60 ml of abs. THF. After the addition had ended, the mixture was stirred at from -20 C. to -30 C. for another 30 min. The mixture was then cooled to -78 C., and a solution of 12.0 g (84.4 mmol) of tert-butyl cyclopropanecarboxylate in 60 ml of abs. THF was added dropwise at this temperature. After 4 h at -78 C., a solution of 15.4 g (70.3 mmol) of 3-bromo-4-chlorobenzaldehyde in 60 ml of abs. THF was added. The reaction mixture was slowly warmed to RT overnight, saturated aqueous ammonium chloride solution was then added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1?10:1). This gave 16.2 g of the target compound (52.5% of theory).LC-MS (Method 4): Rt=1.47 min; m/z=286/288.1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.84-0.99 (m, 2H), 1.02-1.17 (m, 2H), 1.24 (s, 9H), 4.88 (d, 1H), 5.55 (d, 1H), 7.39 (dd, 1H), 7.57 (d, 1H), 7.71 (d, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl cyclopropanecarboxylate, its application will become more common.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/172448; (2012); A1;,
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