methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

Base Information

Chemical Name:methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate
CAS No.:1454588-86-3
Molecular Formula:C₂₉H₃₁NO₃
Molecular Weight:441.57
Hs Code.:

Synonyms:methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

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Chemical Property of methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

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Technology Process of methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

There total 8 articles about methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate 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: 75.0%

: 1454588-83-0
6-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-8-isopropyl-1,1-dimethoxy-11-methylheptaleno[4,5-c]furan-3(1H)-one

: 1454588-86-3
methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃;
DOI:10.1002/hlca.201300137

Reference yield:

: 188635-39-4
dimethyl 1-(chloromethyl)-9-isopropyl-6-methylheptalene-4,5-dicarboxylate

: 1454588-86-3
methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium iodide / acetone / 1 h / 20 °C / Inert atmosphere

2.1: dichloromethane / 0.67 h / 90 - 100 °C / 300 - 450 Torr

3.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

3.2: 12 h / -78 - 20 °C / Inert atmosphere

4.1: lithium hydroxide / methanol; water / 4 h / Reflux

5.1: N,N-dimethyl-formamide; oxalyl dichloride / acetonitrile

6.1: diisobutylaluminium hydride / toluene / -78 °C

With oxalyl dichloride; sodium hexamethyldisilazane; diisobutylaluminium hydride; N,N-dimethyl-formamide; sodium iodide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; acetonitrile; 1.1: |Finkelstein Reaction / 2.1: |Michaelis-Arbuzov Synthesis / 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1002/hlca.201300137

Reference yield:

: 188635-40-7
dimethyl 1-(iodomethyl)-9-isopropyl-6-methylheptalene-4,5-dicarboxylate

: 1454588-86-3
methyl 1-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-4-formyl-9-isopropyl-6-methylheptalene-5-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane / 0.67 h / 90 - 100 °C / 300 - 450 Torr

2.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

2.2: 12 h / -78 - 20 °C / Inert atmosphere

3.1: lithium hydroxide / methanol; water / 4 h / Reflux

4.1: N,N-dimethyl-formamide; oxalyl dichloride / acetonitrile

5.1: diisobutylaluminium hydride / toluene / -78 °C

With oxalyl dichloride; sodium hexamethyldisilazane; diisobutylaluminium hydride; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 1.1: |Michaelis-Arbuzov Synthesis / 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1002/hlca.201300137