Related Products of 58304-65-7,Some common heterocyclic compound, 58304-65-7, name is 1-Chloro-2-methylpropyl propionate, molecular formula is C7H13ClO2, 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 32 2-Butyl-6-(butyloxy)-3-[[2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl]oxy]-5-quinoxalinecarboxylic acid, 2-methyl-1-(1-oxopropoxy)propyl ester A mixture of Example 24 (0.51 g, 0.95 mmol) and silver oxide (1.50 g, 6.5 mmol) in tetrahydrofuran (5 mL) was stirred in the presence of molecular sieves (1.5 g, 4 A powder) at 65 C. for 5 minutes. Propanoic acid, 1-chloro-2-methylpropyl ester (0.4 mL) was then added and the resulting mixture was stirred at 65 C. for 4 hours. It was cooled to 0 C., acidified with 1N aqueous hydrochloric acid (15 mL) and filtered through a Celite pad, and the pad was washed with tetrahydrofuran (50 mL). The combined filtrate solution was washed with brine, dried over sodium sulfate and concentrated. The crude product, which contained a dialkylated analogue, was dissolved in methanol (10 mL) and 5% aqueous sodium hydrogen carbonate (2.0 mL), and the mixture was stirred at room temperature for 1 hour. Solid sodium hydrogen carbonate (0.5 g) was added and the mixture was stirred at room temperature for 5 hours more. It was acidified with 1N aqueous hydrochloric acid and concentrated. The residue was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel eluding with hexane/ethyl acetate/acetic acid (2:1:0.01) to afford Example 32 (0.36 g, 57%) as an oil and the dialkylated compound (0.41 g), contaminated with small amount of impurities. 1 H NMR (CDCl3) delta7.97 (d, J=9.4 Hz, 1H), 7.95 (d, J=7.0 Hz, 1H), 7.59-7.46 (m, 3H), 7.30 (d, J=9.4 Hz, 1H), 7.17 (m, 4H), 6.92 (d, J=5.3 Hz, 1H), 4.15 (m, 2H), 3.06 (t, J=7.6 Hz, 2H), 2.30 (q, J=7.0 Hz, 2H), 2.02 (ot, J=5.1 Hz, 1H), 1.81 (m, 4H), 1.51 (m, 4H), 1.07-0.88 (m, 15H); 13 C NMR (CDCl3) delta173.1, 164.3, 156.1, 155.7, 152.4, 149.3, 140.6, 135.8, 133.9, 130.9, 130.8, 130.6, 130.5, 129.9, 127.8, 123.0, 121.6, 116.9, 114.0, 93.3, 69.1, 33.0, 31.5, 31.1, 29.7, 27.3, 22.5, 18.9, 16.4, 15.9, 13.8, 13.6, 8.7.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-2-methylpropyl propionate, its application will become more common.
Reference:
Patent; E. R. Squibb & Sons, Inc.; US5380719; (1995); A;,
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