These common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, 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. Recommanded Product: Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate
Step A:(Benzyloxycarbonylmethyl)triphenylphosphonium bromide (4.6 g, 9.4 mmol) wasazeotroped twice from toluene, and then suspended in 30 mL dry THF. Potassium hexamethyldisilazide(0.5 M in toluene, 16.8 mL, 8.4 mmol) was added dropwise at room temperature and the yellow solutionwas allowed to stir for 1 h, after which time it became milky white. A solution of 4-carbomethoxybicyclo[2.2.2] octane-1-carboxaldehyde (2-1) (0.50 g, 2.55 mmol) (Adcock, W., Kok, G. B.J. Ore. Chem. 50: 1079-1087 (1985)) and benzoic acid (0.015 g, 0.13 mmol) in 2 mL of dry THF wasprepared and added dropwise by syringe at room temperature. The mixture was heated to 90 C andallowed to stir at reflux temperature, after which time the mixture was diluted with 200 mL of ethylacetate and washed consecutively with 50 mL portions of 1 N HCI (twice), saturated aq. sodiumbicarbonate, and brine. The organic layer was dried using magnesium sulfate, and the solvent wasremoved under reduced pressure. The residue was chromatographed on silica, eluting with a gradient of5% to 10% ethyl acetate in hexane to provide methyl 4-[(lE)-3-(benzyloxy)-3-oxoprop-l-en-l-yl]bicyclo[2.2.2]octane-l-carboxylate (2-2) as a colorless oil. IH NMR (500 MHz, CDCls): 5 7.4 (5H,m), 6.94 (IH, d, J = 17 Hz), 5.77 (IH, d, J = 17 Hz), 5.21 (2H, s), 3.69 (3H, s), 1.86 (6H, m), 1.63 (6H,m) ppm.
The synthetic route of Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK & CO., INC.; WO2006/17542; (2006); A1;,
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