1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone

Base Information

• Chemical Name: 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone
• CAS No.: 489466-58-2
• Molecular Formula: C₂₃H₃₃NO₂Si
• Molecular Weight: 383.606
• Mol file: 489466-58-2.mol

Synonyms:1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone

Chemical Property of 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone

There total 7 articles about 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone 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: 76.0%

3-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-oxo-2-o-tolylpropionic acid methyl ester (489466-56-0) → 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone (489466-58-2)

Guidance literature:

With water; sodium chloride; In dimethyl sulfoxide; at 150 ℃; for 0.5h;

DOI:10.1021/jo026411a

Reference yield:

3-bromo-4-[3-hydroxypropyl]pyridine (229184-01-4) → 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone (489466-58-2)

Guidance literature:

Multi-step reaction with 6 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

6: 76 percent / sodium chloride; water / dimethylsulfoxide / 0.5 h / 150 °C

With 1H-imidazole; 1,3-bis-(diphenylphosphino)propane; potassium trimethylsilonate; water; N-ethyl-N,N-diisopropylamine; sodium chloride; palladium diacetate; In diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 5: Claisen condensation;

DOI:10.1021/jo026411a

Reference yield:

3-Bromo-4-methylpyridin (3430-22-6) → 1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-2-o-tolylethanone (489466-58-2)

Guidance literature:

Multi-step reaction with 7 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

7.1: 76 percent / sodium chloride; water / dimethylsulfoxide / 0.5 h / 150 °C

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

DOI:10.1021/jo026411a

upstream raw materials:

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

3-bromo-4-[3-hydroxypropyl]pyridine

3-Bromo-4-methylpyridin

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

Downstream raw materials:

1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]pyridin-3-yl}-3-(dimethylamino)-2-o-tolylpropenone

4'-(3-hydroxypropyl)-5-(4-methylthiazol-2-yl)-3-o-tolyl-1H-[2,3']bipyridinyl-6-one