In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 11-Bromo-1-undecene, other downstream synthetic routes, hurry up and to see.
Adding a certain compound to certain chemical reactions, such as: 7766-50-9, name is 11-Bromo-1-undecene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7766-50-9, 7766-50-9
The absolute configuration of acetates 5 and 6 was confirmed by alternative chiral synthesis of (2S’,122)-2-acetoxy-12-heptadecene (6) using hydrolytic kinetic resolu- tion (HKR) as the key step (FIG. 6), as follows: 37.5 mmol of butyl lithium (15 ml of 2.5 M solution in hexane) was added under argon at -700C to 3.45 ml (30.0 mmol) of 1-hexyne (9) in 50 ml THF. After stirring 0.5 hours, 5 ml of HMPA and 1.8 ml (8.20 mmol) of 11-bromo-l-undecene (10) was added. The reaction mixture was then warmed to room temperature, stirred 24 hours, quenched with aq. NH4Cl, and extracted with hexane (2 x 50 ml). Combined extracts were washed with brine, dried (anh. MgSO4), and solvents evaporated. The crude product was filtered through 10 g of silica eluting with hexane, yielding 2.05 g of hydrocarbon 11 (85% pure by GC; 7.65 mmol). Without further purification compound 11 was treated with 13.1 mmol of r¡ã-chloroperoxybenzoic acid at 0C in 20 ml of dichloromethane. After 3 hours, the mixture was warmed to room temperature, and after a subsequent 30 min quenched with 50 ml of 2N NaOH and treated with 100 ml of ether. The organic layer was separated, washed with water and brine, and dried (anh. MgSO4). After filtration, removal of solvents in vacuo and flash chromatography, 0.82 g (87% pure by GC; 2.85 mmol) of unsaturated epoxide 12 was obtained. Epoxide 12 in 3 ml of dry THF with 0.030 ml of water was subjected to HKR with freshly prepared R,R-1 Jacobsen catalyst (7,8) [25 mg of (R,R)-N,NN -bis(3 ,5-di-tert-butylsalicylidene)-l ,2-cyclohexanediaminocobalt(II) (Aldrich Chemical Company, Milwaukee, WI) stirred 1 hour with 0.20 ml of toluene and 0.050 ml of acetic acid, and solvents removed in vacuo]. After stirring the reaction mixture 7 days, the recovered (R)-epoxide 13 was separated by flash chromatography [15 g of silica with hexanerether (80:20) as eluent] from the diol 14 and the catalyst, affording 0.4 g of 85% pure (R)-epoxide 13. After removal of solvents, 13 was dissolved in 2 ml of ether and added to a lithium aluminum hydride suspension (10 mmol) in 20 ml of ether. After stirring 3 hours, the reaction mixture was quenched with 2nu NaOH, and the organic phase removed and evaporated. The resulting acetylenic alcohol 15 was hydrogenated in 30 ml of hexane with Lindlar catalyst (5% palladium on calcium carbonate poisoned with lead, 100 mg) and 1 ml of quinoline, yielding 0.350 g of (25′,12Z)-2-hydroxy-12-heptadecene (4). Acetylation of 4, as described above, and further flash column purification gave 0.350 g (1.18 mmol) of (25,12Z)-2-acetoxy-12-heptadecene (6) (yield 14.5% based on 11-bromo-l-undecene 10) with 85% ee.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 11-Bromo-1-undecene, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; GRIES, Regine; KHASKIN, Grigori; DAROOGHEH, Hassan; MART, Cafer; BRITTON, Robert; GRIES, Gerhard; WO2007/79563; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary