5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

Base Information

Chemical Name:5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
CAS No.:1245699-53-9
Molecular Formula:C₁₉H₁₉NO₅S
Molecular Weight:373.43
Hs Code.:

Synonyms:5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

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Chemical Property of 5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

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Technology Process of 5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

There total 6 articles about 5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione 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%

: 1133819-87-0
5-[[4-[2-(3-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-2,4-thiazolidinedione

: 1245699-53-9
5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

Guidance literature:: With [RhCl₂(p-cymene)]2; acetic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; In N,N-dimethyl-formamide; isopropyl alcohol; for 24h; stereoselective reaction; Reflux; Inert atmosphere;
DOI:10.1016/j.bmc.2018.10.033

Reference yield:

: 5000-65-7
2-bromo-3'-methoxyacetophenone

: 1245699-53-9
5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / acetone / 12 h / 20 °C / Inert atmosphere

2: piperidine / ethanol / 12 h / Reflux; Inert atmosphere

3: sodium hydroxide; sodium tetrahydroborate; [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water; N,N-dimethyl-formamide / 18.5 h / 20 °C

4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux

5: [RhCl₂(p-cymene)]2; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; acetic acid; triethylamine / isopropyl alcohol; N,N-dimethyl-formamide / 24 h / Reflux; Inert atmosphere

With piperidine; [2,2]bipyridinyl; sodium tetrahydroborate; [RhCl₂(p-cymene)]2; cobalt(II) chloride hexahydrate; potassium carbonate; acetic acid; triethylamine; sodium hydroxide; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; 2: |Knoevenagel Condensation;
DOI:10.1016/j.bmc.2018.10.033

Reference yield:

: 901414-51-5
4-[2-(3-methoxyphenyl)-2-oxoethoxy]benzaldehyde

: 1245699-53-9
5-[[4-[(2S)-2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione

Guidance literature:: Multi-step reaction with 4 steps

1: piperidine / ethanol / 12 h / Reflux; Inert atmosphere

2: sodium hydroxide; sodium tetrahydroborate; [2,2]bipyridinyl; cobalt(II) chloride hexahydrate / tetrahydrofuran; water; N,N-dimethyl-formamide / 18.5 h / 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux

4: [RhCl₂(p-cymene)]2; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; acetic acid; triethylamine / isopropyl alcohol; N,N-dimethyl-formamide / 24 h / Reflux; Inert atmosphere

With piperidine; [2,2]bipyridinyl; sodium tetrahydroborate; [RhCl₂(p-cymene)]2; cobalt(II) chloride hexahydrate; acetic acid; triethylamine; sodium hydroxide; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; 1: |Knoevenagel Condensation;
DOI:10.1016/j.bmc.2018.10.033