With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.
A reaction vessel was charged with 2,2,6,6-tetramethyltetrahydropyran-4-one (CAS: 1197-66-6, 5.00 g, 32.0 mmol), ethyl cyanoacetate (CAS: 105-56-6, 3.4 ml, 32.0 mmol), morpholine (CAS: 110-91-8, 8.4 ml, 96.0 mmol) and sulfur (CAS: 7704-34-9, 1.03 g, 32.0 mmol) and solvated in ethanol (70 ml). The reaction was set to stir at RT and next heated at 80 C overnight. The reaction was allowed to cool to RT and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and brine. The two phases were separated and the organic phase was washed with brine. The organic phase was dried over MgS04and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel (eluting with 0-40% EtOAc in isohexane) afforded ethyl 2-amino-5,5,7, 7-tetramethyl-4, 7-dihydro-5H-thieno[2,3-c]pyran-3- carboxylate as a yellow oil (7.60 g, yield 84%). The title compound was then synthesized according to the procedure described in Example 1 using ethyl 2-amino-5,5,7,7-tetramethyl-4,7- dihydro-5H-thieno[2,3-c]pyran-3-carboxylate and benzoyl chloride (CAS: 98-88-4) as starting materials (off-white solid, yield 16%).1H NMR (DMSO-d6, 400MHz): d = 13.53 (br s, 1H), 12.40 (s, 1H), 7.97 (d, J=7.5 Hz, 2H), 7.78 – 7.65 (m, 3H), 2.83 (s, 2H), 1.52 (s, 6H), 1.28 (s, 6H). LC/MS (Table 1, Method C) Rt= 2.69 min; MS m/z : 360 [M+H]+.
1197-66-6, The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; ENYO PHARMA; MELDRUM, Eric; DE CHASSEY, Benoit; MACHIN, Peter; LANARO, Roberta; MACLEOD, Calum; MALAGU, Karine, Fabienne; PROISY, Nicolas; VESEY, David, Richard; WINSHIP, Paul, Colin, Michael; CHAMBERS, Mark; PAPARIN, Jean-Laurent; (150 pag.)WO2019/154949; (2019); A1;,
Tetrahydropyran – Wikipedia
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