3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one

Base Information

• Chemical Name: 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one
• CAS No.: 1309567-82-5
• Molecular Formula: C₃₄H₃₇NO₅
• Molecular Weight: 539.671
• Mol file: 1309567-82-5.mol

Synonyms:

Chemical Property of 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one

There total 19 articles about 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one 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:

ethyl 2-cyano-5-(dimethylamino)-3-methoxypenta-2,4-dienoate → 3-(8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one + 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one (1309567-82-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic acid / water / Reflux

2.1: N-Bromosuccinimide / -18 °C / Reflux; Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.2: 16 h / 60 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 60 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 - -20 °C / Inert atmosphere

5.2: 0.17 h / -78 - 0 °C / Inert atmosphere

6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 72 h / Inert atmosphere; Darkness

With N-Bromosuccinimide; n-butyllithium; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; 6.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.201007671

Reference yield:

(R,E)-ethyl 2,4-dimethylhex-2-enoate (474828-49-4) → 3-(8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one + 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one (1309567-82-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

2.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: lithium chloride / acetonitrile / -20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

5.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C / Inert atmosphere

6.1: lithium chloride / acetonitrile / -20 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

8.1: 4-methyl-2-morpholinone; tetrapropylammonium perruthennate / dichloromethane / 1 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

9.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 72 h / Inert atmosphere; Darkness

With 4-methyl-2-morpholinone; manganese(IV) oxide; tetrapropylammonium perruthennate; lithium hydroxide monohydrate; diisobutylaluminium hydride; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination / 6.1: Horner-Wadsworth-Emmons olefination / 6.2: Horner-Wadsworth-Emmons olefination / 9.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.201007671

Reference yield:

ethyl 5-bromo-4-methoxy-2-oxo-1,2-dihydropyridine-3-carboxylate (1309567-73-4) → 3-(8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one + 3-((R,2E,4E,6E,8E)-8,10-dimethyldodeca-2,4,6,8-tetraenoyl)-4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)pyridin-2(1H)-one (1309567-82-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: 16 h / 60 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 60 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 - -20 °C / Inert atmosphere

3.2: 0.17 h / -78 - 0 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 72 h / Inert atmosphere; Darkness

With n-butyllithium; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; 4.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1002/anie.201007671

upstream raw materials:

ethyl 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1-((2-(trimethylsilyl) ethoxy)methyl)-1,2-dihydropyridine-3-carboxylate

ethyl 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-((2-(trimethylsilyl)ethoxy)methoxy)nicotinate

ethyl 4-methoxy-5-(4-((4-methoxybenzyl)oxy)phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

(8R,2E,4E,6E)-6,8-dimethyldeca-2,4,6-trienal

Refernces