3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

Base Information

Chemical Name:3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone
CAS No.:436844-94-9
Molecular Formula:C₂₂H₂₄N₂O₃
Molecular Weight:364.444
Hs Code.:

Synonyms:3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

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Chemical Property of 3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

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Technology Process of 3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

There total 9 articles about 3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone 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: 38.0%

: 436844-91-6
4-(1,2-dihydro-1-methyl-2-oxo-3-pyridinyl)butanal

: 117068-71-0
2-(benzyloxy)-6-bromopyridine

: 436844-94-9
3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

Guidance literature:: 2-(benzyloxy)-6-bromopyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

4-(1,2-dihydro-1-methyl-2-oxo-3-pyridinyl)butanal; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/jo025565n

Reference yield:

: 436844-92-7
4-(2-fluoro-3-pyridinyl)-3-butyn-1-ol

: 436844-94-9
3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / H₂ / 10percent Pd/C / ethanol; ethyl acetate / 34 h / 760.05 Torr

2.1: 91 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3.1: CHCl₃ / 15 h / Heating

3.2: 83 percent / Et₃N; AcOH / CHCl₃; ethanol / 1 h / Heating

4.1: 95 percent / K₂CO₃ / methanol; H₂O / 1 h

5.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

6.2: 38 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With dmap; n-butyllithium; oxalyl dichloride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; ethyl acetate; 5.1: Swern oxidation;
DOI:10.1021/jo025565n

Reference yield:

: 56826-62-1
1-methyl-5,6,7,8-tetrahydroquinolinium iodide

: 436844-94-9
3-[4-(6-benzyloxy-2-pyridinyl)-4-hydroxybutyl]-1-methyl-2(1H)-pyridinone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 40 percent / 2N NaOH / K₃Fe(CN)6 / 4.25 h / 0 - 50 °C

2.1: 95 percent / conc. H₂SO₄ / 18 h / 20 °C

3.1: 83 percent / DIBAL / tetrahydrofuran; hexane / 2 h / 0 °C

4.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

5.2: 38 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With sodium hydroxide; n-butyllithium; oxalyl dichloride; sulfuric acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; hexane; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/jo025565n