The origin of a common compound about 15799-79-8

According to the analysis of related databases, 15799-79-8, the application of this compound in the production field has become more and more popular.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Methoxy-N,N-dimethylaniline

[0092] (R)-3-(4-Dimethylamino-2-methoxy-phenyl)-pentanal (Table 1, entry 3): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.200 equiv), CH2Cl2 (0.50 ml), HCl (as a 4N solution in 1,4-dioxane, 25.0 uL, 0.100 mmol, 0.200 equiv), and N,N-dimethyl-m-anisidine (73.3 uL, 0.500 mmol, 1.00 equiv). The solution was cooled to -50o C. before pentenal (98.0 uL, 1.00 mmol, 2.00 equiv) was added. After 62 h, the reaction mixture was subjected directly to silica gel chromatography. Elution with 20% EtOAc in hexanes followed by concentration and removal of residual pentenal under vacuum afforded the product as a colorless oil in 68% yield (79.5 mg, 0.338 mmol); 88% ee. IR (film) 2959, 2926, 2871, 2839, 2800, 2721, 1718, 1616, 1569, 1517, 1351, 1237, 1136, 1034, 979.5, 812.9 cm-1;1H NMR (300 MHz, CDCl3) ?9.63 (t, J=2.8 Hz, 1H, CHO), 6.97 (d, J=8.2 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.3 Hz, 1H, ArH), 6.26 (d, J=2.5 Hz, 1H, ArH), 3.81 (s, 3H, OCH3), 3.40 (dt, J=7.3, 7.4 Hz, 1H, ArCH), 2.94 (s, 6H, N(CH3)2), 2.66 (dd, J=2.7, 7.4 Hz, 2H, CH2CO), 1.72-1.61 (m, 2H, CH2CH3), 0.83 (t, J=7.4 Hz, 3H, CH2CH3); 13C NMR (75 MHz, CDCl3) 203.8, 158.2, 150.6, 128.4, 119.8, 105.0, 96.5, 55.5, 49.7, 1.1, 34.9, 28.4, 12.4. HRMS (CI) exact mass calcd for (C14H21NO2) requires m/z 236.1650 for [M+H]+, found m/z 236.1649. [?]D=-18.9 (c=0.970, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (3.0% ethanol/hexanes, 1 mL/min); S isomer tr=11.5 min, R isomer tr=12.4 min.

According to the analysis of related databases, 15799-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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