Electric Literature of 506-43-4 , The common heterocyclic compound, 506-43-4, name is (9Z,12Z)-Octadeca-9,12-dien-1-ol, molecular formula is C18H34O, 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.
To a solution of the alcohol 1 (26.6 g, 100 mmol) in 5 dichloromethane (100 mL), 6 triethylamine (13.13 g, 130 mmol) was added and this solution was cooled in an ice-bath. To this cold solution, a solution of 7 mesyl chloride (12.6 g, 110 mmol) in dichloromethane (60 mL) was added dropwise and after the completion of the addition, the reaction mixture was allowed to warm to ambient temperature and stirred overnight. The TLC of the reaction mixture showed the completion of the reaction. The reaction mixture was diluted with dichloromethane (200 mL), washed with water (200 mL), satd. 8 NaHCO3 (200 mL), brine (100 mL) and dried (NaSO4). The organic layer was concentrated to get the crude product which was purified by column chromatography (silica gel) using 0-10% 9 Et2O in hexanes. The pure product fractions were combined and concentrated to obtain the pure product (10 2) as colorless oil (30.6 g, 89%). 1H NMR (CDCl3, 400 MHz) delta=5.42-5.21 (m, 4H), 4.20 (t, 2H), 3.06 (s, 3H), 2.79 (t, 2H), 2.19-2.00 (m, 4H), 1.90-1.70 (m, 2H), 1.06-1.18 (m, 18H), 0.88 (t, 3H). 13C NMR (CDCl3) delta=130.76, 130.54, 128.6, 128.4, 70.67, 37.9, 32.05, 30.12, 29.87, 29.85, 29.68, 29.65, 29.53, 27.72, 27.71, 26.15, 25.94, 23.09, 14.60. MS. Molecular weight calculated for C19H36O3S, Cal. 344.53, Found 343.52 (M-H-).
The synthetic route of 506-43-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ALNYLAM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL CO. LTD; Manoharan, Muthiah; Rajeev, Kallanthottathil G.; Nair, Jayaprakash K.; Jayaraman, Muthusamy; Matsumoto, Satoru; (92 pag.)US9701623; (2017); B2;,
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