1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

Base Information

Chemical Name:1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester
CAS No.:467242-39-3
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

1-{2-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

Synonyms:1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

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Chemical Property of 1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

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Technology Process of 1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

There total 9 articles about 1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl 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: 83.0%

: 30889-20-4
methyl cyclohexa-2,5-diene-1-carboxylate

: 467242-35-9
tert-butyl-{[(2R)-2-(2-iodoethyl)-2-methylcyclopentyl]oxy}dimethylsilane

: 467242-39-3
1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

Guidance literature:: methyl cyclohexa-2,5-diene-1-carboxylate; tert-butyl-{[(2R)-2-(2-iodoethyl)-2-methylcyclopentyl]oxy}dimethylsilane; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at 50 ℃; for 3h;
DOI:10.1016/S0040-4039(02)00570-1

Reference yield:

: 7424-82-0,99031-95-5,94089-46-0
methyl (1R)-3-(1-methyl-2-oxocyclopentyl)propanoate

: 467242-39-3
1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / potassium hydroxide / methanol / 16 h / 20 °C

2.1: 84 percent / iodine; Pb(OAc)4 / CCl₄ / 1 h / 80 °C / Irradiation

3.1: 65 percent / NaBH₄ / ethanol / 3 h / 20 °C

4.1: 96 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

5.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: 83 percent / DMPU / tetrahydrofuran / -78 - 50 °C

With 1H-imidazole; lead(IV) acetate; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; iodine; diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; 2.1: Barton-Koch reaction;
DOI:10.1002/ejoc.200600429

Reference yield:

: 918813-46-4
(2R)-2-(2-iodoethyl)-2-methylcyclopentanone

: 467242-39-3
1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-ethyl}-cyclohexa-2,5-dienecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 65 percent / NaBH₄ / ethanol / 3 h / 20 °C

2.1: 96 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

3.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: 83 percent / DMPU / tetrahydrofuran / -78 - 50 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.1002/ejoc.200600429