Synthetic Route of 18448-47-0, These common heterocyclic compound, 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, 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.
2.5 M n-Butyllithium in hexanes (7.25 mL, 18.1 mmol) was added dropwise to a cooled (ice water bath) mixture of S-(-)-N-benzyl-alpha-methylbenzylamine (15.1 mmol) in THF (60 mL). After stirring for 30 minutes the mixture was cooled to -95 C. (liquid nitrogen/acetone bath). A solution of methyl-1-cyclohexenecarboxylate (12.5 mmol) in THF (10 mL) was added to the chilled reaction mixture dropwise. After 1.5 hours the liquid nitrogen/acetone bath was replaced with a dry ice/acetone bath. The chilled reaction mixture was stirred for 2 hours and was quenched by the dropwise addition of 2,6-di-tert-butylphenol (25.2 mmol) in THF (20 mL). The reaction mixture was warmed to room temperature then concentrated in vacuo. The residue was dissolved in 100 mL of 50% dichloromethane in ether. The mixture was washed twice with brine. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (solvent gradient: ethyl aceteate/hexanes, 2% to 5%) to afford the desired product (2.25 g) as a yellow oil in 54% yield.: 1H NMR (300 Mz, CDCl3) delta 7.38 (d, 4 H, J=7.3), 7.28 (m, 5 H), 7.18 (m, 2 H), 3.93 (m, 2 H), 3.77-3.68 (m, 1 H), 3.60 (s, 3 H), 2.68 (m, 1 H), 2.50 (m, 1 H), 2.14 (m, 1 H), 1.81 (m, 1 H), 1.70-1.52 (m, 4 H), 1.35-1.12 (m, 2 H) 1.27 (d, 3 H, J=7.0); MS m/e 352 (M+H)+.
Statistics shows that Methyl cyclohex-1-enecarboxylate is playing an increasingly important role. we look forward to future research findings about 18448-47-0.
Reference:
Patent; Marcin, Lawrence R.; Higgins, Mendi A.; US2005/113442; (2005); A1;,
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