3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

Base Information

Chemical Name:3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester
CAS No.:637362-49-3
Molecular Formula:C₁₇H₃₀O₃Si
Molecular Weight:310.509
Hs Code.:

3-[1-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

Synonyms:3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

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Chemical Property of 3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

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Technology Process of 3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

There total 3 articles about 3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic 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: 88.0%

: 67-56-1
methanol

: 637362-48-2
3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-acrylic acid ethyl ester

: 637362-49-3
3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

Guidance literature:: With magnesium; at 0 ℃;
DOI:10.1016/j.tetlet.2003.09.215

Reference yield:

: 74269-63-9
(1-Benzyloxymethyl-cyclohexa-2,5-dienyl)-methanol

: 637362-49-3
3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 10 h / 20 °C

2: 94 percent / Li; liq. NH₃ / tetrahydrofuran / 0.33 h / -20 °C

3: 90 percent / Dess-Martin reagent; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

4: 99 percent / t-BuOK / tetrahydrofuran / -78 - 0 °C

5: 88 percent / Mg / 0 °C

With 1H-imidazole; dmap; potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Dess-Martin oxidation / 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2003.09.215

Reference yield:

: 637362-45-9
(1-benzyloxymethyl-cyclohexa-2,5-dienylmethoxy)-tert-butyl-dimethyl-silane

: 637362-49-3
3-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / Li; liq. NH₃ / tetrahydrofuran / 0.33 h / -20 °C

2: 90 percent / Dess-Martin reagent; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

3: 99 percent / t-BuOK / tetrahydrofuran / -78 - 0 °C

4: 88 percent / Mg / 0 °C

With potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; In tetrahydrofuran; dichloromethane; 2: Dess-Martin oxidation / 3: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2003.09.215