3-(triphenylstannyl)propyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 3-(triphenylstannyl)propyl 4-methylbenzenesulfonate
• CAS No.: 799278-89-0
• Molecular Formula: C₂₈H₂₈O₃SSn
• Molecular Weight: 563.305
• Mol file: 799278-89-0.mol

Synonyms:

Chemical Property of 3-(triphenylstannyl)propyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(triphenylstannyl)propyl 4-methylbenzenesulfonate

There total 2 articles about 3-(triphenylstannyl)propyl 4-methylbenzenesulfonate 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: 81.0%

3-(triphenylstannyl)-1-propanol (33304-76-6) + p-toluenesulfonyl chloride (98-59-9) → (3-chloropropyl)triphenylstannane (35843-43-7) + 3-(triphenylstannyl)propyl 4-methylbenzenesulfonate (799278-89-0)

Guidance literature:

In pyridine; soln. of CH3C6H4SO2Cl (1 equiv.) in pyridine added slowly to Sn compd.; stirred at room temp. for 4 h; H2O added; acidified with 50% H2SO4-H2O; aq. layer extd. (CH2Cl2); combined org. layers dried (MgSO4); solvent distd. off; volatiles removed under high vac.; sepd. by chromy. (SiO2, petroleum ether-EtOAc from 5:1 to 1:1, EtOAc); elem. anal.;

DOI:10.1016/j.jorganchem.2004.06.065

Reference yield:

triphenylstannane (892-20-6) → 3-(triphenylstannyl)propyl 4-methylbenzenesulfonate (799278-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2'-azobis(isobutyronitrile) / 3 h / 80 - 90 °C / Schlenk technique; Inert atmosphere; Glovebox

2: triethylamine; trimethylamine hydrochloride / dichloromethane / 2 h / Schlenk technique; Glovebox

With 2,2'-azobis(isobutyronitrile); trimethylamine hydrochloride; triethylamine; In dichloromethane;

DOI:10.1002/chem.201703453

Reference yield: 92.0%

3-(triphenylstannyl)propyl 4-methylbenzenesulfonate (799278-89-0) + 1-tert-butyl-1,3-cyclopentadiene (84857-63-6) → 1,4-di-tert-butyltricyclo[5.2.1.0(1,7)]deca-3,8-diene + 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene (799278-90-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; paraffin; under exclusion of moisture and air; t-BuCpH added dropwise to NaH suspn. in paraffin at -78°C; warmed to room temp. under stirring; cooled to -78°C; soln. of Sn compd. in THF added dropwise; warmed to room temp. for 12 h; volatiles removed; sepd. by chromy. (SiO2, gradient petroleum ether-ethyle acetate 5:1, 1:1);

DOI:10.1016/j.jorganchem.2004.06.065

upstream raw materials:

3-(triphenylstannyl)-1-propanol

p-toluenesulfonyl chloride

triphenylstannane

Downstream raw materials:

4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene