3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one

Base Information

• Chemical Name: 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one
• CAS No.: 1357016-46-6
• Molecular Formula: C₂₆H₂₂O₆
• Molecular Weight: 430.457
• Mol file: 1357016-46-6.mol

Synonyms:

Chemical Property of 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one

There total 11 articles about 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-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: 84.0%

(2S,3S,3aS)-3a-ethoxy-6,8-dimethoxy-1-(4-methoxyphenyl)-2-phenyl-3,3a-dihydro-2H-cyclopenta[b]benzofuran-3-ol → 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one (1357016-46-6)

Guidance literature:

With oxygen; for 12h; Inert atmosphere;

DOI:10.1021/jo202366c

Reference yield:

4,6-dihydroxy-2-(4-methoxyphenyl)benzofuran-3(2H)-one (117828-32-7) → 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one (1357016-46-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / acetone / 0.5 h / Reflux; Inert atmosphere

2.1: tetrahydrofuran / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: 4-methyl-morpholine; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 3 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: potassium hydride / tetrahydrofuran; mineral oil / Inert atmosphere

5.2: Inert atmosphere

6.1: tert.-butyl lithium / diethyl ether; hexane / -40 °C / Inert atmosphere

6.2: Inert atmosphere

6.3: 6 h / 20 °C / Inert atmosphere

7.1: lithium triethylborohydride / tetrahydrofuran / -30 °C / Inert atmosphere

8.1: oxygen / 12 h / Inert atmosphere

With 4-methyl-morpholine; osmium(VIII) oxide; n-butyllithium; tert.-butyl lithium; oxygen; potassium hydride; lithium triethylborohydride; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; water; acetone; mineral oil; tert-butyl alcohol; 6.3: Nazarov cyclization;

DOI:10.1021/jo202366c

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → 3-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-5-phenyl-2H-pyran-2-one (1357016-46-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: water; ethyl acetate / 20 h / Inert atmosphere

2.1: hydrogenchloride / diethyl ether / 1 h / 0 °C / Inert atmosphere

2.2: 3 h / 112 °C / Inert atmosphere

3.1: potassium carbonate / acetone / 0.5 h / Reflux; Inert atmosphere

4.1: tetrahydrofuran / 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: 4-methyl-morpholine; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 3 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere

7.1: potassium hydride / tetrahydrofuran; mineral oil / Inert atmosphere

7.2: Inert atmosphere

8.1: tert.-butyl lithium / diethyl ether; hexane / -40 °C / Inert atmosphere

8.2: Inert atmosphere

8.3: 6 h / 20 °C / Inert atmosphere

9.1: lithium triethylborohydride / tetrahydrofuran / -30 °C / Inert atmosphere

10.1: oxygen / 12 h / Inert atmosphere

With 4-methyl-morpholine; hydrogenchloride; osmium(VIII) oxide; n-butyllithium; tert.-butyl lithium; oxygen; potassium hydride; lithium triethylborohydride; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; water; ethyl acetate; acetone; mineral oil; tert-butyl alcohol; 2.1: Hoesch reaction / 8.3: Nazarov cyclization;

DOI:10.1021/jo202366c

upstream raw materials:

1-[4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-yl]-3-phenylprop-2-yn-1-ol

3-(1-ethoxy-3-phenylprop-2-ynyl)-4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran

4,6-dimethoxy-2-(4-methoxyphenyl)-3-vinylbenzofuran

4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-carboxaldehyde