Application of 5617-32-3 , The common heterocyclic compound, 5617-32-3, name is 3,6,9,12,15,18-Hexaoxaicosane-1,20-diol, molecular formula is C14H30O8, its 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.
6.2 3,6,9,12,15,18,21-Heptaoxahexacos-25-en-1-ol (2) To an anhydrous THF solution of NaH (0.39 g of 45percent in mineral oil, 10.1 mmol) was added heptaethylene glycol (1, 3 g, 9.2 mmol) drop wise at 4 °C. After 30 min, 1-bromopentene (1.18 mL, 10.1 mmol) was added slowly to the above solution. The reaction mixture allowed to warm to room temperature and then stirred under N2 for 14 h. The reaction was quenched by addition of methanol at 0 °C, the solvent was evaporated and 200 mL of water was added to the residue which was then extracted with ethyl acetate (100 mL, 3*). The organic layers were washed with brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure. Purification by flash column chromatography over silica gel with 1percent methanol in dichloromethane gave pure color less oil 2: Rf: 0.41 (4percent MeOH in DCM); yield: 1.86 g, 52percent, 1H NMR (400 MHz; CDCl3) delta 5.82 (ddtd, J = 16.9, 10.2, 6.6, 1.9 Hz, 1H), 5.07-4.90 (m, 2H), 3.79-3.53 (m, 28H), 3.47 (td, J = 6.7, 1.8 Hz, 2H), 2.61 (t, J = 6.2 Hz, 1H), 2.11 (dtt, J = 8.0, 6.7, 1.4 Hz, 2H), 1.74-1.62 (m, 2H); 13C NMR (CDCl3; 100 MHz) delta 132.2, 114.6, 77.4, 76.9, 76.6, 70.6, 70.5, 70.0, 69.9, 50.6, 30.2, 28.7; MS m/z [M+H]+ calcd for C19H39O8 394.2, found 394.2; MS m/z [M+Na]+ calcd for C19H38O8Na 417.2, found 417.2.
The synthetic route of 5617-32-3 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Biswas, Souvik; Medina, Scott H.; Barchi, Joseph J.; Carbohydrate Research; vol. 405; (2015); p. 93 – 101;,
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