1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

Base Information

Chemical Name:1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid
CAS No.:1410839-64-3
Molecular Formula:C₁₇H₃₀O₃Si
Molecular Weight:310.509
Hs Code.:

Synonyms:1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

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Chemical Property of 1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

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Technology Process of 1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

There total 2 articles about 1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid 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%

: 62627-31-0
1-(hydroxymethyl)-2,5-cyclohexadiene-1-carboxylic acid

: 13154-24-0
triisopropylsilyl chloride

: 1410839-64-3
1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

Guidance literature:: 1-(hydroxymethyl)-2,5-cyclohexadiene-1-carboxylic acid; triisopropylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.333333h; Inert atmosphere;

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 5h; Inert atmosphere;
DOI:10.1002/ejoc.201301065

Reference yield:

: C₁₃H₁₈O₄

: 1410839-64-3
1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hydroxide / tetrahydrofuran / 1.5 h / 0 - 20 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 0 - 20 °C

With 1H-imidazole; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ol302908a

Reference yield:

: 1410839-64-3
1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid

: C₂₁H₃₁NO₉

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1,4-bis(9-O-dihydroquinidine)phthalazine; N-Bromosuccinimide / chloroform; hexane / 12 h / -40 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / -40 °C / Inert atmosphere

3.1: potassium carbonate / 1 h / 0 °C

4.1: dmap / acetonitrile / 10 h / 0 - 20 °C / Inert atmosphere

5.1: tert.-butylhydroperoxide / ethyl acetate; decane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

5.2: 48 h / Molecular sieve; Inert atmosphere

5.3: 4 h / Molecular sieve; Inert atmosphere

6.1: Trimethyl borate / methanol / 0.33 h / -78 °C / Inert atmosphere

6.2: 0.33 h / -78 °C / Inert atmosphere

7.1: diethylazodicarboxylate; triphenylphosphine / toluene / 0.75 h / 0 - 20 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

9.1: trifluoroacetic acid / dichloromethane / 5 h / 0 °C / Inert atmosphere

10.1: sodium hydride / methanol; mineral oil / 0.5 h / 0 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 12 h / 60 °C / Inert atmosphere

12.1: 5%-palladium/activated carbon; triethylamine; hydrogen / ethyl acetate / 2.5 h / 20 °C

With tert.-butylhydroperoxide; dmap; N-Bromosuccinimide; Trimethyl borate; 5%-palladium/activated carbon; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; chloroform; ethyl acetate; 1,2-dichloro-ethane; toluene; acetonitrile; mineral oil; 7.1: |Mitsunobu Displacement;
DOI:10.1002/ejoc.201301065