methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

Base Information

Chemical Name:methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate
CAS No.:189272-32-0
Molecular Formula:C₂₂H₃₀O₃
Molecular Weight:342.478
Hs Code.:

Synonyms:methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

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Chemical Property of methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

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Technology Process of methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

There total 5 articles about methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-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: 94.0%

: 189272-18-2
2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-carbaldehyde

: 19945-56-3
methyl 4-diethylphosphono-3-methyl-2-butenoate

: 189272-32-0
methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

Guidance literature:: methyl 4-diethylphosphono-3-methyl-2-butenoate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; cooling;

2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-carbaldehyde; In tetrahydrofuran; hexane; cooling;
DOI:10.1016/j.bmc.2006.04.043

Reference yield:

: 109769-41-7
2-(1-ethynyl-2,6,6-trimethylcyclohexene)-1,3,2-benzodioxaborole

: 189272-32-0
methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / potassium hydroxide / Pd(PPh₃)4 / benzene; H₂O / Heating

2.1: 97 percent / diisobutyl aluminium hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

3.1: 92 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / -78 - 20 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / cooling

4.2: 94 percent / tetrahydrofuran; hexane / cooling

With potassium hydroxide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; water; benzene; 1.1: Suzuki coupling / 3.1: Swern oxidation / 4.2: Horner-Emmons olefination;
DOI:10.1016/j.bmc.2006.04.043

Reference yield:

: 177734-77-9
methyl 4-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydrofuran-3-carboxylate

: 189272-32-0
methyl (E,E)-3-methyl-5-[2-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl]-2,5-dihydrofuran-3-yl]penta-2,4-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / potassium hydroxide / Pd(PPh₃)4 / benzene; H₂O / Heating

2.1: 97 percent / diisobutyl aluminium hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

3.1: 92 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / -78 - 20 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / cooling

4.2: 94 percent / tetrahydrofuran; hexane / cooling

With potassium hydroxide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; water; benzene; 1.1: Suzuki coupling / 3.1: Swern oxidation / 4.2: Horner-Emmons olefination;
DOI:10.1016/j.bmc.2006.04.043