(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester

Base Information

• Chemical Name: (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester
• CAS No.: 202194-34-1
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.457
• Mol file: 202194-34-1.mol

Synonyms:(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester

Chemical Property of (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester

There total 8 articles about (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester 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: 18.0%

ethyl (2E)-4-(diethoxyphosphoryl)crotonate (42516-28-9) + (1S,3R,4R)-1-Acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane (70224-50-9) → (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester (202194-34-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.) -40 deg C, 1 h, 2.) -40 deg C to r.t., 6 h;

Reference yield:

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0) → (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester (202194-34-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / MeLi, HMPA / diethyl ether; tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 35 min

2: 71 percent / NaBH₄ / ethanol / 13 h / 0 - 20 °C

3: Et₃N / diethyl ether / 3 h / 0 °C

4: DBU / diethyl ether / 4 h

5: 3 M aq. KOH / ethanol / 1 h / Heating

6: tetrahydrofuran; diethyl ether / 0.67 h / 0 °C

7: CuI, LiAlH₄ / tetrahydrofuran / 1 h

8: 18 percent / LDA / tetrahydrofuran; hexane / 1.) -40 deg C, 1 h, 2.) -40 deg C to r.t., 6 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; methyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; hexane;

Reference yield:

(4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-enecarboxylic acid (202194-37-4) → (2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid ethyl ester (202194-34-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether / 0.67 h / 0 °C

2: CuI, LiAlH₄ / tetrahydrofuran / 1 h

3: 18 percent / LDA / tetrahydrofuran; hexane / 1.) -40 deg C, 1 h, 2.) -40 deg C to r.t., 6 h

With copper(l) iodide; lithium aluminium tetrahydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

upstream raw materials:

ethyl (2E)-4-(diethoxyphosphoryl)crotonate

(1S,3R,4R)-1-Acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene

(4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohexen-1-yl methyl ketone

Downstream raw materials:

fuscol