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. Quality Control of tert-Butyl cyclopropanecarboxylate
Example 25ATert-Butyl 1-(prop-2-en-1-yl)cyclopropanecarboxylate 9.9 ml (70.32 mmol) of diisopropylamine were initially charged in 35 ml of THF, 28.1 ml (70.32 mmol) of a 2.5 M solution of n-butyllithium in n-hexane were added at -40 C. and the mixture was stirred for 30 min. The reaction mixture was then cooled to -78 C., and a solution of 10 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 5 ml of THF was added dropwise. The mixture was stirred at -78 C. for 4 h, and a solution of 5.8 ml (66.81 mmol) of allyl bromide in 5 ml of THF was then added dropwise. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully. The mixture was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. This gave 10.7 g (83.5% of theory) of the target compound.GC-MS (Method 1): Rt=2.5 min; m/z=126 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta=5.82 (m, 1H), 4.98 (d, 2H), 2.21 (d, 2H), 1.37 (s, 9H), 0.99 (q, 2H), 0.69 (q, 2H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87661-20-9, its application will become more common.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); A1;,
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