{5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl ester

Base Information

• Chemical Name: {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl ester
• CAS No.: 158090-21-2
• Molecular Formula: C₂₂H₃₃NO₅S
• Molecular Weight: 423.574

Synonyms:{5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl ester

Chemical Property of {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl ester

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Technology Process of {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl ester

There total 7 articles about {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl 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: 72.0%

ethyl iodoacetae (623-48-3) + (E)-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)isothiazolidine 1,1-dioxide (158090-19-8) → {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ6-isothiazolidin-2-yl}-acetic acid ethyl ester (158090-21-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/jm9906015

Reference yield:

2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-dioxolane (74222-81-4) → {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ6-isothiazolidin-2-yl}-acetic acid ethyl ester (158090-21-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h

1.2: 80 percent / tetrahydrofuran; dimethylformamide / 1 h

2.1: 100 percent / aq. HCl / acetone / 1 h

3.1: diisopropylamine; BuLi; hexamethylphosphamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.1: p-TsOH / toluene / 0.5 h / Heating

5.1: 41 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 72 percent / K₂CO₃ / dimethylformamide / 3 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; titanium tetrachloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Addition / 4.1: Dehydration / 5.1: debenzylation / 6.1: Condensation;

DOI:10.1021/jm9906015

Reference yield:

4-Methoxymethoxy-3,5-di-tert-butylbenzaldehyde (151166-75-5) → {5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ6-isothiazolidin-2-yl}-acetic acid ethyl ester (158090-21-2)

Guidance literature:

Multi-step reaction with 4 steps

1: diisopropylamine; BuLi; hexamethylphosphamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

2: p-TsOH / toluene / 0.5 h / Heating

3: 41 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 0 °C

4: 72 percent / K₂CO₃ / dimethylformamide / 3 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; titanium tetrachloride; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Addition / 2: Dehydration / 3: debenzylation / 4: Condensation;

DOI:10.1021/jm9906015

upstream raw materials:

ethyl iodoacetae

(E)-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)isothiazolidine 1,1-dioxide

2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-dioxolane

4-Methoxymethoxy-3,5-di-tert-butylbenzaldehyde

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