3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

Base Information

Chemical Name:3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone
CAS No.:561068-92-6
Molecular Formula:C₂₈H₃₃NO₅
Molecular Weight:463.574
Hs Code.:

Synonyms:3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

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Chemical Property of 3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

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Technology Process of 3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

There total 10 articles about 3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone 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: 71.0%

: 182344-15-6
(3,5-di-tert-butyl-4-hydroxyphenyl)boronic acid

: 561068-86-8
3-acetyl-N-benzyloxy-5-bromo-4-hydroxy-2(1H)-pyridone

: 561068-92-6
3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

Guidance literature:: With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 12h; Heating;
DOI:10.1016/j.tet.2006.01.090

Reference yield:

: 1139-52-2
4-bromo-2,6-di-tert-butylphenol

: 561068-92-6
3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuLi / tetrahydrofuran; hexane / 1 h / 25 °C

1.2: 45 percent / triisopropyl borate / tetrahydrofuran; hexane / 12 h / 25 °C

2.1: 71 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran / 12 h / Heating

With tert.-butyl lithium; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; 2.1: Suzuki reaction;
DOI:10.1016/j.tet.2006.01.090

Reference yield:

: 30204-31-0
3-(benzyloxyamino)propanoic acid methyl ester

: 561068-92-6
3-acetyl-N-benzyloxy-5-[3,5-di-tert-butyl-4-hydroxyphenyl]-4-hydroxy-2(1H)-pyridone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 84 percent / 4-(dimethylamino)pyridine; triethylamine / tetrahydrofuran / -78 - 0 °C

2.1: LiOH*H₂O / tetrahydrofuran; H₂O / 2 h / 25 °C

3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 12 h / 25 °C

3.2: 86 percent / NaH / tetrahydrofuran / 5 h / 25 °C

4.1: 25 percent / Pb(OAc)4 / benzene / 20 h / 70 °C

5.1: 72 percent / Br₂ / CH₂Cl₂ / 12 h / Heating

6.1: 71 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / tetrahydrofuran / 12 h / Heating

With lead(IV) acetate; dmap; lithium hydroxide; bromine; sodium carbonate; triethylamine; 1,1'-carbonyldiimidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; benzene; 6.1: Suzuki reaction;
DOI:10.1016/j.tet.2006.01.090