methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

Base Information

Chemical Name:methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate
CAS No.:289677-51-6
Molecular Formula:C₂₁H₂₉NO₃Si
Molecular Weight:371.552
Hs Code.:

Synonyms:methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

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Chemical Property of methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

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Technology Process of methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

There total 1 articles about methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate 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: 63.0%

: 619-42-1
4-methoxycarbonylphenyl bromide

: 3-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridine

: 289677-51-6
methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

Guidance literature:: 4-methoxycarbonylphenyl bromide; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

3-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pyridine; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 12h;
DOI:10.1016/S0968-0896(00)00051-1

Reference yield: 91.0%

: 289677-51-6
methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

: 289677-52-7
methyl 4-[5-hydroxyethyl-3-pyridinyl]benzoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 3h;
DOI:10.1016/S0968-0896(00)00051-1

Reference yield:

: 289677-51-6
methyl 4-[5-[[[(1,1-dimethylethyl)silyl]oxy]ethyl]-3-pyridinyl]benzoate

: N-{4-[5-[(2,4-diamino-6(1H)-pyrimidinon-5-yl)ethyl]-3-pyridinyl]benzoyl}-L-glutamic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / Bu₄NF / tetrahydrofuran / 3 h / 25 °C

2: 87 percent / SOCl₂ / CH₂Cl₂ / 3 h / 50 °C

3: 63 percent / K₂CO₃ / dimethylformamide / 3 h / 70 °C

4: 56 percent / NaOEt / ethanol / 12 h / 45 °C

5: 91 percent / LiOH; H₂O / methanol / 12 h / 25 °C

6: 48 percent / NaHCO₃; EDCI / dimethylformamide / 12 h / 25 °C

7: 83 percent / trifluoroacetic acid / CH₂Cl₂ / 0 - 25 °C

With lithium hydroxide; thionyl chloride; tetrabutyl ammonium fluoride; water; sodium ethanolate; sodium hydrogencarbonate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: silyl ether cleavage / 2: Chlorination / 3: Alkylation / 4: cyclocondensation / 5: Hydrolysis / 6: Acylation / 7: ester cleavage;
DOI:10.1016/S0968-0896(00)00051-1