(3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-methanol

Base Information

• Chemical Name: (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-methanol
• CAS No.: 223579-21-3
• Molecular Formula: C₂₂H₃₇NO₅S
• Molecular Weight: 427.605

Synonyms:(3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-methanol

Chemical Property of (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-methanol

Chemical Property:

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Technology Process of (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-methanol

There total 5 articles about (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-methanol 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: 55.0%

N-ethyl-1,2-isothiazolidine-1,1-dioxide (73343-04-1) + 4-Methoxymethoxy-3,5-di-tert-butylbenzaldehyde (151166-75-5) → (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ6-isothiazolidin-5-yl)-methanol (223579-21-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1021/jm9906015

Reference yield:

2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-dioxolane (74222-81-4) → (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ6-isothiazolidin-5-yl)-methanol (223579-21-3)

Guidance literature:

Multi-step reaction with 3 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: 55 percent / diisopropylamine; BuLi; hexamethylphosphamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydride; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone; 1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Addition;

DOI:10.1021/jm9906015

Reference yield:

N1-ethyl-3-chloro-1-propanesulfonamide (216487-29-5) → (3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-(2-ethyl-1,1-dioxo-1λ6-isothiazolidin-5-yl)-methanol (223579-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaH / tetrahydrofuran / 0.5 h / Heating

2: 55 percent / diisopropylamine; BuLi; hexamethylphosphamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydride; diisopropylamine; In tetrahydrofuran; hexane; 1: Cyclization / 2: Addition;

DOI:10.1021/jm9906015

upstream raw materials:

N-ethyl-1,2-isothiazolidine-1,1-dioxide

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

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

N₁-ethyl-3-chloro-1-propanesulfonamide

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