Ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate
• CAS No.: 134653-98-8
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.272
• Hs Code.: 2933399090
• Mol file: 134653-98-8.mol

Synonyms:6-tert-butyl-4-hydroxy-nicotinic acid ethyl ester;

Chemical Property of Ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Chemical Property:

• Boiling Point: 324.8±42.0 °C(Predicted)
• PKA: 10.09±0.69(Predicted)
• PSA: 59.42000
• Density: 1.105±0.06 g/cm3(Predicted)
• LogP: 2.26140
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Ethyl6-tert-Butyl-4-oxo-1,4-dihydro-pyridine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

There total 2 articles about Ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

ethyl 6-tert-butyl-4-oxo-4H-pyran-3-carboxylate (134653-81-9) → 6-tert-butyl-4-hydroxy-nicotinic acid ethyl ester (134653-98-8,1143519-19-0)

Guidance literature:

ethyl 6-tert-butyl-4-oxo-4H-pyran-3-carboxylate; With ammonium acetate; acetic acid; In ethanol; water; at 95 ℃; for 0.5h;

With sodium hydroxide; In water;

Reference yield: 68.0%

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6,51145-57-4) + 2,2-dimethylpropanoic anhydride (1538-75-6) → ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (1143519-19-0,134653-98-8)

Guidance literature:

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate; 2,2-dimethylpropanoic anhydride; With lithium hexamethyldisilazane; In tetrahydrofuran; at -75 - -50 ℃; for 0.333333h;

With acetic acid; In tetrahydrofuran; at 20 - 60 ℃; for 0.5h;

DOI:10.1021/op300294g

Reference yield:

ethyl 6-(tert-butyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (1143519-19-0,134653-98-8) → ethyl 6-tert-butyl-4-(2,4,6-trimethylphenoxy)pyridine-3-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1.1: trichlorophosphate / 1.5 h / 110 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 20 °C

2.2: 1 h / 60 °C

With sodium hydride; trichlorophosphate; In tetrahydrofuran; mineral oil;

upstream raw materials:

ethyl 6-tert-butyl-4-oxo-4H-pyran-3-carboxylate

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate

2,2-dimethylpropanoic anhydride

Downstream raw materials:

6-tert-butyl-4-ethoxy-nicotinic acid

rac-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(3-methanesulfonyl-propyl)-piperazin-1-yl]-methanone

2-{1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-acetamide

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