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, Dimethyl cyclohexane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.
Application of 62638-06-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 62638-06-6, name is Dimethyl cyclohexane-1,3-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
EXAMPLE 25; l,3-Dicarbomethoxybicyclo[3.2.1]octane; A cooled (-67C) solution of dry diisopropylamine (ll.OmL, 78 mmol) in anhydrous THF (60mL) in a 3-neck 500mL round bottom flask equipped with magnetic stirring, addition funnel, and gas inlet/thermometer was treated via syringe with 2.4N n-butyllithium/hexane (30mL, 72 mmol) at a rate to keep the pot temperature <-50C, warmed to 0C for 5 minutes, then recooled (-67 C). l,3-Dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (DMPU, 36.3mL, 300 mmole, dried over molecular seives) was added dropwise so as to keep pot temp < -60 C, then a solution of dimethyl cyclohexane-l,3-dicarboxylate (12.01g, 60 mmol) in anhydrous THF (20mL) was likewise added dropwise. After lh at -67 C, a solution of l-bromo-2-chloroethane (12.05g, 84 mmol) in anhydrous THF (15mL) was added dropwise so as to keep pot temp <-50 C, and the mixture was warmed to room temperature over 1.5h and stirred at room temperature for 18h, then cooled on an ice bath and quenched with saturated aqueous ammonium chloride (50mL). The organic solvent was removed in vacuo and the aqueous residue was extracted with 9:1 hexane/ethyl acetate (150mL, lOOmL, 2X50mL). The combined organic extracts were washed with water (lOOmL), dried (MgS04), and concentrated in vacuo. The residue was dissolved in methylene chloride and passed through a pad of alumina in a 60mL fritted glass funnel (eluted with methylene chloride) to afford 15.36g (97% of theoretical) of a pale yellow oil which was essentially the desired intermediate with minor impurities.A solution of l-(2-chloroethyl)-l,3-dicarbomethoxycyclohexane (all of semi-purified from 60 mmol dimethyl cyclohexane-l,3-dicarboxylate) and DMPU (36.3mL, 300 mmol) in anhydrous THF (150mL) under nitrogen in a 500mL 3-neck flask equipped with magnetic stirring, addition funnel, and gas inlet/thermometer was cooled to -67C. Meanwhile, a cooled (-67C) solution of dry diisopropylamine (ll.OmL, 78 mmol) in anhydrous THF (75mL) under nitrogen was treated via syringe with 2.4N n-butyllithium/hexane (30mL, 72 mmol), the mixture was warmed to 0C for 5 min, then recooled (-67C). The LDA solution was cannulated in portions (~6) into the other solution at a rate to keep pot temperature <-60 C, then the mixture was stirred at -67 C for 30 min, warmed to room temperature over 1.5h, then stirred at room temperature for 18h,. cooled on an ice bath and quenched with saturated aqueous ammonium chloride (50mL). The organic solvent was removed in vacuo and the aqueous residue was extracted with 9:1 hexane/ethyl acetate (150mL, lOOmL, 2X50mL). The combined organic extracts were washed with water (lOOmL), dried (MgS04), and concentrated in vacuo. The residue was dissolved in methylene chloride and passed through a pad of alumina in a 60mL fritted glass funnel (eluted with methylene chloride) to afford crude subject material (9.52g) as a pale yellow oil. Chromatography on silica gel (~400cc) eluted with 40%, then 50% methylene chloride/hexane, then methylene chloride alone, then 10% ethyl acetate/methylene chloride afforded 8.32g (61% for two steps from dimethyl cyclohexane-l,3-dicarboxylate) purified subject material as a very pale yellow oil. [M+H]+=226.9. *H NMR (CDC13) 8 3.66 (s,6H), 2.20-2.30 (m,lH), 2.00-2.10 (m,2H), 1.70-1.80 (m,5H), 1.55-1.65 (m,4H).
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, Dimethyl cyclohexane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ROYALTY, Susan Marie; BURNS, James Ford; SCICINSKI, Jan Jozef; JAGDMANN, JR., Gunnar Erik; FOGLESONG, Robert James; GRIFFIN, Kellee Renee; DYAKONOV, Tatyana; MIDDLEMISS, David; WO2006/12395; (2006); A2;,
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