ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate

Base Information

• Chemical Name: ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate
• CAS No.: 40244-49-3
• Molecular Formula: C₁₇H₂₆O₂
• Molecular Weight: 262.392
• Mol file: 40244-49-3.mol

Synonyms:ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate

Chemical Property of ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate

There total 2 articles about ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate 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:

(2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide (141208-06-2) → ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate (40244-49-3) + ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate (40244-66-4) + (2Z,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (29789-62-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene; tetrahydrofuran / 20 h / 0 - 20 °C

2.1: sodium hydride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

2.2: 16 h / 100 °C / Inert atmosphere

3.1: riboflavin / acetonitrile / 24 h / 20 °C / UV-irradiation; Sealed tube; Inert atmosphere

With sodium hydride; riboflavin; In tetrahydrofuran; 1,4-dioxane; toluene; acetonitrile; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acs.orglett.9b03842

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate (40244-49-3) + ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate (40244-66-4) + (2Z,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (29789-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

1.2: 16 h / 100 °C / Inert atmosphere

2.1: riboflavin / acetonitrile / 24 h / 20 °C / UV-irradiation; Sealed tube; Inert atmosphere

With sodium hydride; riboflavin; In 1,4-dioxane; acetonitrile; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acs.orglett.9b03842

Reference yield:

ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoate (40244-49-3) + diisopropylamine (108-18-9) + methyl iodide (74-88-4) → methyl-(2Z,4E)-2,3-dimethyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoate (181303-19-5)

Guidance literature:

With n-butyllithium; sodium methylate; lithium diisopropyl amide; In tetrahydrofuran; methanol; water;

upstream raw materials:

(2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide

(E)-β-ionone

Downstream raw materials:

methyl-(2Z,4E)-2,3-dimethyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoate