dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

Base Information

Chemical Name:dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate
CAS No.:1228753-05-6
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

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Chemical Property of dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

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Technology Process of dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

There total 7 articles about dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate 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: 90.0%

: 1228753-04-5
dimethyl 2-(5-methoxy-2-(2-methylallyl)benzylidene)malonate

: 1774-47-6
trimethylsulfoxonium iodide

: 1228753-05-6
dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

Guidance literature:: trimethylsulfoxonium iodide; With sodium hydride; dimethyl sulfoxide; at 20 ℃; Inert atmosphere;

dimethyl 2-(5-methoxy-2-(2-methylallyl)benzylidene)malonate; In dimethyl sulfoxide; at 20 ℃; for 20h; Inert atmosphere;
DOI:10.1002/anie.201000563

Reference yield: 82.0%

: dimethyl 2-(2-iodo-5-methoxyphenyl)cyclopropane-1,1-dicarboxylate

: 167773-10-6
4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane

: 1228753-05-6
dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

Guidance literature:: dimethyl 2-(2-iodo-5-methoxyphenyl)cyclopropane-1,1-dicarboxylate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane; In tetrahydrofuran; Inert atmosphere; Reflux;
DOI:10.1021/acs.orglett.5b01927

Reference yield:

: 13421-00-6
5-chloro-2-iodo-benzoic acid

: 1228753-05-6
dimethyl 2-(5-methoxy-2-(2-methylallyl)phenyl)cyclopropane-1,1-dicarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C

2.1: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.2: 2 h / 0 - 20 °C

4.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.2: Suzuki-Miyaura Coupling / Inert atmosphere; Reflux

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; boron trifluoride diethyl etherate; silica gel; cesium fluoride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination / 5.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.orglett.5b01927