Application of 169751-72-8 , The common heterocyclic compound, 169751-72-8, name is tert-Butyl 14-hydroxy-3,6,9,12-tetraoxatetradecan-1-oate, molecular formula is C14H28O7, 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.
4-Toluenesulfonyl chloride (2.49 g, 13.1 mmol) was added to an ice-cooled solution of tert- butyl 14-hydroxy-3,6,9,12-tetraoxatetradecan-l-oate (2.96 g, 7.68 mmol) in pyridine (30 mL). The reaction was stirred at room temperature for 5 hours. The reaction mixture was partitioned between ethyl acetate (50 mL) and 2 M aq. HCI (40 mL). The organic extract was separated, washed with 2M aq HCI (40 mL), followed by saturated sodium bicarbonate (50 mL) and brine (50 mL). The organic extract was then dried and concentrated under reduced pressure and the product was purified by chromatography on silica 330g, using a gradient elution from 0-100% methyl tert-butyl ether in cyclohexane to yield tert-butyl 14-(tosyloxy)- 3,6,9,12-tetraoxatetradecan-l-oate (2.17 g, 4.50 mmol, 59 % yield), as a colourless oil. 1H NMR (400 MHz, CDCI3 ) delta ppm 1.47 (s, 9H), 2.45 (s, 3H), 3.58 (s, 4H), 3.63 (m, 4H), 3.68 (m, 8H), 4.01 (s, 2H), 4.16 (m, 2H), 7.34 (d, 2H, J=8.3Hz), 7.78 (d, 2H, J=8.3Hz) . MS (m/z) 463
The synthetic route of 169751-72-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
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