(2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester
CAS No.:606122-83-2
Molecular Formula:C₂₈H₃₉FO₃
Molecular Weight:442.614
Hs Code.:

Synonyms:(2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

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Chemical Property of (2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

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Technology Process of (2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

There total 10 articles about (2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-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: 94.0%

: triethyl 3-methyl-4-phosphonocrotonate

: 330935-86-9
1-[3,5-di-iso-propyl-2-(3-fluoropropoxy)benzene]-2-formylcyclopentene

: 606122-83-2
(2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: triethyl 3-methyl-4-phosphonocrotonate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

1-[3,5-di-iso-propyl-2-(3-fluoropropoxy)benzene]-2-formylcyclopentene; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2.5h;
DOI:10.1021/jm020401k

Reference yield:

: 2934-05-6
2,4-diisopropylphenol

: 606122-83-2
(2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / N-iodosuccinimide; p-toluenesulfonic acid / CH₂Cl₂ / 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 97 percent / dimethylformamide / 3 h / 0 - 20 °C

3.1: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: diethyl ether; tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

4.1: 6.6 g / aq. HCl / diethyl ether; tetrahydrofuran; hexane / 0.5 °C

5.1: 89 percent / Pd(PPh₃)4; aq. Na₂CO₃ / toluene; ethanol / 15 h / 90 °C

6.1: 99 percent / aq. HCl / tetrahydrofuran / 65 h / 20 °C

7.1: 99 percent / NaAlH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

8.1: 85 percent / CsF / dimethylformamide / 20 °C

9.1: 100 percent / tetrapropylammonium perruthenate; 4-methylmorpholine-N-oxide / CH₂Cl₂ / 1.5 h / 20 °C

10.1: DMPU; n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

10.2: 94 percent / DMPU / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrapropylammonium perruthennate; sodium aluminum tetrahydride; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; cesium fluoride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Suzuki coupling / 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm020401k

Reference yield:

: 330935-02-9
2,4-di-iso-propyl-6-iodophenol

: 606122-83-2
(2E,4E)-5-{2-[2-(3-Fluoro-propoxy)-3,5-diisopropyl-phenyl]-cyclopent-1-enyl}-3-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 97 percent / dimethylformamide / 3 h / 0 - 20 °C

2.1: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: diethyl ether; tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

3.1: 6.6 g / aq. HCl / diethyl ether; tetrahydrofuran; hexane / 0.5 °C

4.1: 89 percent / Pd(PPh₃)4; aq. Na₂CO₃ / toluene; ethanol / 15 h / 90 °C

5.1: 99 percent / aq. HCl / tetrahydrofuran / 65 h / 20 °C

6.1: 99 percent / NaAlH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

7.1: 85 percent / CsF / dimethylformamide / 20 °C

8.1: 100 percent / tetrapropylammonium perruthenate; 4-methylmorpholine-N-oxide / CH₂Cl₂ / 1.5 h / 20 °C

9.1: DMPU; n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: 94 percent / DMPU / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrapropylammonium perruthennate; sodium aluminum tetrahydride; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; cesium fluoride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Suzuki coupling / 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm020401k