Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate

Base Information

• Chemical Name: Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate
• CAS No.: 162792-95-2
• Molecular Formula: C₂₄H₃₄O₂
• Molecular Weight: 354.533
• Mol file: 162792-95-2.mol

Synonyms:Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate

Chemical Property of Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate

There total 7 articles about Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate 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:

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) + (E,E)-3-<3-Methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>propan-2-one (162792-92-9) → Ethyl (E,E,Z)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate (162792-94-1) + Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate (162792-95-2)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1248/cpb.42.2659

Reference yield:

2,6,6-trimethylcyclohex-1-enecarbaldehyde (432-25-7) → Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate (162792-95-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 61 percent / LDA / tetrahydrofuran / -78 °C / 1.) 30 min, 2.) 1 h

2: tetrahydrofuran / -78 deg C, 70 min; -50 deg C, 20 min; 0 deg C, 20 min

3: 15percent aq. H₂SO₄ / tetrahydrofuran / 0.33 h / 0 °C

4: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

5: 83 percent / DBU / toluene / 1 h / Heating

6: 1.) LDA, 2.) AcOH, aq. NaOAc / 1.) THF, benzene, r.t., 30 min; THF, r.t.; 2 h, 2.) THF, r.t., 5 h

7: LDA / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) r.t., 30 min

With dmap; sulfuric acid; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/a606719k

Reference yield:

(E)-3-Methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enone (162792-90-7) → Ethyl (E,E,E)-3-methyl-4-<3-methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>but-2-enoate (162792-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA, 2.) AcOH, aq. NaOAc / 1.) THF, benzene, r.t., 30 min; THF, r.t.; 2 h, 2.) THF, r.t., 5 h

2: LDA / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) r.t., 30 min

With sodium acetate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/a606719k

upstream raw materials:

trimethylsilanyl-acetic acid ethyl ester

(E,E)-3-<3-Methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enylidene>propan-2-one

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(E)-3-Methyl-4-<(2,6,6-trimethylcyclohex-1-enyl)methylene>cyclohex-2-enone