Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks
[0095] (S)-4-Benzoyloxy-3-(4-dimethylamino-2-methoxy-phenyl)-butyraldehyde (Table 1, entry 4): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tertbutyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.100 equiv), N,N-dimethyl-anisidine hydrochloride (18.8 mg, 0.100 mmol., 0.100 equiv), CHCl3 (1.00 ml), and N,N-dimethyl-m-anisidine (132 uL, 0.900 mmol, 0.900 equiv). The solution was cooled to -20o C. before 4-benzoyloxy-crotonaldehyde (0.380, 2.00 mmol, 2.00 equiv) was added as a solid. After 24 h, the reaction mixture was subjected directly to silica gel chromatography. Gradient elution with 10-25% EtOAc in hexanes followed by concentration and removal of residual pentenal under vacuum afforded the product as a colorless oil in 89% yield (304 mg, 0.889 mmol); 92% ee. IR (film) 2940, 2892, 2836, 2724, 1719, 1615, 1518, 1273, 1240, 1117, 712.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.74 (t, J=2.1 Hz, 1H, CHO), 8.01 (ddd, J=0.6, 1.1, 6.3 Hz., 2H, ArH), 7.58-7.40 (m, 3H, ArH), 7.08 (d, J=8.2 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.25 (d, J=2.4 Hz, 1H, ArH), 4.51 (dd, J=5.5, 10.7 Hz, 1H, CH2O), 4.42 (dd, J=8.2, 10.7 Hz, 1H, CH2O), 4.08-3.98 (m, 1H, ArCH), 3.83 (s, 3H, OCH3), 2.98-2.80 (m, 2H, CH2CO), 2.95 (s, 6H, N(CH3); 13C NMR (75 MHz, CDCl3) 202.2, 166.6, 158.2, 151.3, 133.1, 130.3, 129.8, 129.0, 128.6, 115.6, 104.9, 96.3, 67.9, 55.4, 46.3, 50.0, 33.5. HRMS (CI) exact mass calcd for (C20H23NO4) requires m/z 342.1705 for [M+H]+, found m/z 342.1705. [?]D =-16.9 (c=0.751, 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 (10% ethanol/hexanes, 1 mL/min); R isomer tr=15.2 min, S isomer tr=24.0 min.
The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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