Electric Literature of 3618-04-0, A common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 oxalyl chloride (6 mL, 68.8 mmol) in DCM (100 mL) at -78° C. was added dropwise a solution of DMSO (6.4 mL, 90 mmol) in DCM (20 mL). The mixture was stirred at this temperature for 15 min before the dropwise addition of a solution of ethyl 4-hydroxycyclohexane carboxylate (4.8 mL, 30 mmol) in DCM (20 mL). The mixture was stirred at -78° C. for 3 h before addition of TEA (29.3 mL, 210 mmol) in DCM (20 mL). The mixture was then gradually warmed to rt, washed with a sat. aq. NH4Cl solution and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography over SiO2 (Hex/EA 1:1) to give the title ketone (4.6 g, 90percent yield) as a colourless oil. 1H NMR (CDCl3) delta: 4.19 (q, J=7.1 Hz, 2H); 2.80-2.70 (m, 1H); 2.55-2.45 (m, 2H); 2.40-2.30 (m, 2H); 2.25-2.10 (m, 2H); 2.05-2.00 (m, 2H); 1.29 (t, J=7.1 Hz, 3H).
The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; US2009/105232; (2009); A1;,
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