methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

Base Information

Chemical Name:methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate
CAS No.:1357495-95-4
Molecular Formula:C₂₁H₂₃NO₆S
Molecular Weight:417.483
Hs Code.:

Synonyms:methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

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Chemical Property of methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

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Technology Process of methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

There total 4 articles about methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-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: 47.0%

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

: 1357495-93-2
methyl 7-oxo-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

: 1357495-95-4
methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

methyl 7-oxo-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere; Reflux;
DOI:10.1016/j.tetlet.2011.12.013

Reference yield:

: 208928-20-5
methyl 2-methoxy-4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carboxylate

: 1357495-95-4
methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: zinc(II) chloride / dichloromethane / 1.33 h / 0 °C / Inert atmosphere

2.1: sodium hydride / diethyl ether; dimethyl sulfoxide / 0.17 h / 0 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C / Inert atmosphere

2.3: 0.33 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.2: 5.2 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4.2: 5 h / 20 °C / Inert atmosphere; Reflux

With sodium hexamethyldisilazane; sodium hydride; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 4.1: Horner-Wadsworth-Emmons reaction / 4.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2011.12.013

Reference yield:

: 67201-30-3
methyl 4-oxocyclohex-2-ene-1-carboxylate

: 1357495-95-4
methyl 7-(ethoxycarbonylmethylene)-2-p-toluenesulfonyl-4,5,6,7-tetrahydro-2H-isoindole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / diethyl ether; dimethyl sulfoxide / 0.17 h / 0 °C / Inert atmosphere

1.2: 4 h / 0 - 20 °C / Inert atmosphere

1.3: 0.33 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.2: 5.2 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.2: 5 h / 20 °C / Inert atmosphere; Reflux

With sodium hexamethyldisilazane; sodium hydride; sodium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 3.1: Horner-Wadsworth-Emmons reaction / 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2011.12.013