2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

Base Information

Chemical Name:2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester
CAS No.:109333-90-6
Molecular Formula:C₂₄H₂₈N₂O₄
Molecular Weight:408.497
Hs Code.:

Synonyms:2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

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Chemical Property of 2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

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Technology Process of 2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

There total 9 articles about 2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl 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: 98.0%

: 109307-34-8
3-{1-[2-(5-Methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

: 109333-90-6
2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

Guidance literature:: With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 23 ℃; for 1.2h;
DOI:10.1021/ja00249a043

Reference yield:

: 54162-19-5
2,4-Cyclohexadien-1-carbonsaeure-methylester

: 109333-90-6
2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -60 deg C, 30 min, 2.) THF, from -60 to 0 deg C, 14 h

2: 3percent NaOH / tetrahydrofuran; H₂O; methanol / 16 h / 23 °C

3: 1.) 1,1'-carbonylimidazol / 1.) THF, 23 deg C, 18 h, 2.) THF, -78 deg C, 1 h

4: 98 percent / p-toluenesulfonyl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.2 h / 23 °C

With sodium hydroxide; 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja00249a043

Reference yield:

: 109307-30-4
4-Ethynyl-5-methyl-6,7-dihydro-benzofuran

: 109333-90-6
2-Diazo-3-{1-[2-(5-methyl-6,7-dihydro-benzofuran-4-yl)-ethyl]-cyclohexa-2,4-dienyl}-3-oxo-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) disiamylborane, 2.) potassium carbonate, 3percent hydrogen peroxyde / 1.) THF, 5 h, 0 deg C, 2.) water, 5 min, 20 deg C

2: sodium borohydride / methanol / 0.08 h / 0 °C

3: 84 percent / triphenylphosphine, imidazole, iodine / 0.25 h / 23 °C

4: 1.) LDA / 1.) THF, -60 deg C, 30 min, 2.) THF, from -60 to 0 deg C, 14 h

5: 3percent NaOH / tetrahydrofuran; H₂O; methanol / 16 h / 23 °C

6: 1.) 1,1'-carbonylimidazol / 1.) THF, 23 deg C, 18 h, 2.) THF, -78 deg C, 1 h

7: 98 percent / p-toluenesulfonyl azide, 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.2 h / 23 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; 4-toluenesulfonyl azide; dihydrogen peroxide; iodine; bis-(1,2-dimethylpropyl)borane; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja00249a043