(Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate

Base Information

• Chemical Name: (Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate
• CAS No.: 1421357-64-3
• Molecular Formula: C₂₃H₃₆N₂O₆Si
• Molecular Weight: 464.634

Synonyms:(Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate

Chemical Property of (Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate

Chemical Property:

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Technology Process of (Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate

There total 2 articles about (Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate 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: 83.0%

methyl 3-((tert-butyldimethylsilyl)oxy)-2-diazopent-3-enoate (1246011-22-2) + ethyl 2-(N-(4-methoxyphenyl)hydrazono)acetate (545445-35-0) → (Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate (1421357-64-3)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1021/jo302696y

Reference yield:

4-methoxyphenylhydrazine hydrochloride (19501-58-7) → (Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate (1421357-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / Inert atmosphere

1.2: 12.5 h / 0 - 20 °C / Inert atmosphere

2.1: dirhodium tetraacetate / dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

With dirhodium tetraacetate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo302696y

Reference yield:

(Z)-6-ethyl 1-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-[(E)-(4-methoxyphenyl)diazenyl]-4-methylhex-2-enedioate (1421357-64-3) → ethyl 5-[(tert-butyl-dimethylsilyl)oxy]-5-(2-methoxy-2-oxoethyl)-1-(4-methoxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylate

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo302696y

upstream raw materials:

methyl 3-((tert-butyldimethylsilyl)oxy)-2-diazopent-3-enoate

ethyl 2-(N-(4-methoxyphenyl)hydrazono)acetate

4-methoxyphenylhydrazine hydrochloride

Downstream raw materials:

ethyl 5-(2-methoxy-2-oxoethyl)-1-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylate

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