(2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

Base Information

Chemical Name:(2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate
CAS No.:1269259-99-5
Molecular Formula:C₁₈H₂₄O₃
Molecular Weight:288.387
Hs Code.:

Synonyms:(2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

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Chemical Property of (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

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Technology Process of (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

There total 6 articles about (2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-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: 85.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 62924-31-6
1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one

: 1269259-99-5
(2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

1-(2,5,6-trimethyl-4-methoxyphenyl)-but-1-en-3-one; In tetrahydrofuran; at 0 ℃; for 6h; Reflux;
DOI:10.1002/chem.201403024

Reference yield:

: 41891-54-7
diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate

: 54344-92-2
2,3,6-trimethyl-4-methoxy-benzaldehyde

: ethyl (2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

: 1269259-99-5
(2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

Guidance literature:: diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; hexanes; at 0 ℃; for 0.666667h; Horner-Wadsworth-Emmons reaction;

2,3,6-trimethyl-4-methoxy-benzaldehyde; In tetrahydrofuran; hexanes; at -78 - 0 ℃; optical yield given as %de;
DOI:10.1016/j.ejmech.2010.12.008

Reference yield:

: 65527-85-7
ethyl (E)-4-hydroxy-3-methyl-2-butenoate

: ethyl (2Z,4E)-5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

: 1269259-99-5
(2E,4E)-ethyl 5-(-4-methoxy-2,3,6-trimethylphenyl)-3-methylpenta-2,4-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrachloromethane; triphenylphosphine / acetonitrile / 1 h / 25 °C

2.1: 2.5 h / 150 °C

3.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium / tetrahydrofuran; hexanes / 0.67 h / 0 °C / Horner-Wadsworth-Emmons reaction

3.2: -78 - 0 °C

With tetrachloromethane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexanes; acetonitrile; 2.1: Michaelis-Arbuzov reaction / 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.ejmech.2010.12.008