3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Base Information

Chemical Name:3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester
CAS No.:489466-56-0
Molecular Formula:C₂₅H₃₅NO₄Si
Molecular Weight:441.643
Hs Code.:

Synonyms:3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

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Chemical Property of 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

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Technology Process of 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

There total 5 articles about 3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic 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:

: 229184-01-4
3-bromo-4-[3-hydroxypropyl]pyridine

: 489466-56-0
3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

2: 88 percent / N-ethyldiisopropylamine; 1,3-bis(diphenylphosphino)propane / palladium(II) acetate / dimethylformamide / 20 h / 20 - 95 °C

3: 89 percent / potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C

4: dimethylformamide / 1.5 h / 50 °C

5: 1.69 g / 60percent sodium hydride / dimethylformamide / 3.25 h / -10 - 20 °C

With 1H-imidazole; 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; N-ethyl-N,N-diisopropylamine; palladium diacetate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Claisen condensation;
DOI:10.1021/jo026411a

Reference yield:

: 3430-22-6
3-Bromo-4-methylpyridin

: 489466-56-0
3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisopropylamine; butyllithium / tetrahydrofuran; hexane / 0.75 h / 5 - 50 °C

1.2: 78 percent / tetrahydrofuran; hexane / 0.5 h / -20 - 0 °C

2.1: 100 percent / imidazole / CH₂Cl₂ / 17 h / 20 °C

3.1: 88 percent / N-ethyldiisopropylamine; 1,3-bis(diphenylphosphino)propane / palladium(II) acetate / dimethylformamide / 20 h / 20 - 95 °C

4.1: 89 percent / potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C

5.1: dimethylformamide / 1.5 h / 50 °C

6.1: 1.69 g / 60percent sodium hydride / dimethylformamide / 3.25 h / -10 - 20 °C

With 1H-imidazole; n-butyllithium; 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; diisopropylamine; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Claisen condensation;
DOI:10.1021/jo026411a

Reference yield:

: 380830-44-4
3-bromo-4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridine

: 489466-56-0
3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / N-ethyldiisopropylamine; 1,3-bis(diphenylphosphino)propane / palladium(II) acetate / dimethylformamide / 20 h / 20 - 95 °C

2: 89 percent / potassium trimethylsilanolate / diethyl ether / 48 h / 20 °C

3: dimethylformamide / 1.5 h / 50 °C

4: 1.69 g / 60percent sodium hydride / dimethylformamide / 3.25 h / -10 - 20 °C

With 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; N-ethyl-N,N-diisopropylamine; palladium diacetate; In diethyl ether; N,N-dimethyl-formamide; 4: Claisen condensation;
DOI:10.1021/jo026411a