1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene

Base Information

• Chemical Name: 1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene
• CAS No.: 201035-87-2
• Molecular Formula: C₃₁H₃₃NO₂Si
• Molecular Weight: 479.694
• Mol file: 201035-87-2.mol

Synonyms:1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene

Chemical Property of 1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene

There total 1 articles about 1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene 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: 89.0%

2-(2-iodophenyl)acetonitrile (40400-15-5) + tert-Butyl-diphenyl-[3-(5-tributylstannanyl-furan-2-yl)-propoxy]-silane → 1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene (201035-87-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(97)10437-3

Reference yield: 75.0%

1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene (201035-87-2) → 1-[5'-(3''-hydroxy-propan-1''-yl)-2'-furanyl]-2-methylcyano-benzene (944382-73-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;

DOI:10.1016/S0040-4039(97)10437-3

Reference yield:

1-[5-'-(3''-tert-butyldiphenylsilyloxy-propan-1''-yl)-2'-furanyl]-2-methylcyanobenzene (201035-87-2) → 1-[5'-(3''-bromo-propan-1''-yl)-2'-furanyl]-2-methylcyano-benzene (944382-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / tetra-n-butylammonium fluoride; p-toluenesulphonic acid / tetrahydrofuran / 12 h / 0 - 20 °C

2: 85 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.5 h / 0 °C

With carbon tetrabromide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b703373g

upstream raw materials:

2-(2-iodophenyl)acetonitrile

Downstream raw materials:

1-[5'-(3''-hydroxy-propan-1''-yl)-2'-furanyl]-2-methylcyano-benzene

C₁₅H₁₅BrO₂

1-[5'-(3''-bromo-propan-1''-yl)-2'-furanyl]-2-methylcyano-benzene

1-[5'-(3''-bromo-propan-1''-yl)-2'-furanyl]-2-(2'''-oxo-but-3'''-yn-1'''-yl)benzene

Refernces

• 1、 Jones, Philip,Li, Wan-Sheung,Pattenden, Gerald,Thomson, Nicholas M.. "An exploration of the scope for radical-mediated transannular Diels-Alder reactions in polycycle synthesis". . p. 9069 - 9072. Retrieved 1997.