Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate

Base Information

• Chemical Name: Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate
• CAS No.: 339090-38-9
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353

Synonyms:Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate

Chemical Property of Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate

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Technology Process of Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate

There total 2 articles about Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate 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: 97.0%

methyl 4‐(2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrol‐1‐yl)benzoate (40349-49-3) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate (339090-38-9)

Guidance literature:

In toluene; at 70 ℃; for 2h;

DOI:10.1039/b004098n

Reference yield:

(Z)-4-((4-(methoxycarbonyl)phenyl)amino)-4-oxobut-2-enoic acid (125407-30-9) → Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate (339090-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: HMDS; ZnBr₂ / benzene / 3 h / Heating

2: 97 percent / toluene / 2 h / 70 °C

With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide; In toluene; benzene; 2: Diels-Alder reaction;

DOI:10.1039/b004098n

Reference yield: 60.0%

Methyl 4-(5,6-dimethyl-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl)benzoate (339090-38-9) → Methyl 4-(3,5-dimethyl-8,10-dioxo-4-oxa-9-azatricyclo[5.3.0.03,5]decan-9-yl)benzoate + Methyl 4-(3,5-dimethyl-8,10-dioxo-4-oxa-9-azatricyclo[5.3.0.03,5]decan-9-yl)benzoate

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20 ℃; for 3h;

DOI:10.1039/b004098n

upstream raw materials:

methyl 4‐(2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrol‐1‐yl)benzoate

2,3-dimethyl-buta-1,3-diene

(Z)-4-((4-(methoxycarbonyl)phenyl)amino)-4-oxobut-2-enoic acid

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