ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate

Base Information

• Chemical Name: ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate
• CAS No.: 1450740-53-0
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343
• Mol file: 1450740-53-0.mol

Synonyms:ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate

Chemical Property of ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate

There total 2 articles about ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate 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: 80.0%

O-methyldehydrozingerone (15001-27-1,60234-90-4) + propynoic acid ethyl ester (623-47-2) → ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate (1450740-53-0)

Guidance literature:

propynoic acid ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

O-methyldehydrozingerone; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2013.06.044

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate (1450740-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: morpholin-4-ium 2,2,2-trifluoroacetate / 80 °C / Sealed tube

2.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

With morpholin-4-ium 2,2,2-trifluoroacetate; lithium diisopropyl amide; In tetrahydrofuran; 1.1: |Aldol Condensation;

DOI:10.1016/j.bmc.2013.06.044

Reference yield: 72.0%

ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate (1450740-53-0) → 5-methyl-5-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-2,5-dihydrofuran-2-one (1450740-27-8)

Guidance literature:

ethyl (5E)-4-hydroxy-4-methyl-6-(3,4-dimethoxyphenyl)hex-5-en-2-ynoate; With quinoline; hydrogen; In methanol; at 20 ℃; for 3h;

In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2013.06.044

upstream raw materials:

3,4-dimethoxy-benzaldehyde

O-methyldehydrozingerone

propynoic acid ethyl ester

Downstream raw materials:

5-methyl-5-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-2,5-dihydrofuran-2-one