(Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene

Base Information

• Chemical Name: (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene
• CAS No.: 865999-31-1
• Molecular Formula: C₂₆H₃₆BNO₃
• Molecular Weight: 421.388
• Mol file: 865999-31-1.mol

Synonyms:(Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene

Chemical Property of (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene

There total 5 articles about (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene 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: 55.0%

1,1-bis(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-2-phenyl-1-butene (865999-18-4) + [2-(4-iodophenoxy)ethyl]dimethylamine (93790-54-6) → (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene (865999-31-1)

Guidance literature:

With potassium hydroxide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tri-tert-butyl phosphine; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/ja054484g

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + E-(Et)(C6H5)CC(4-Me2N(CH2)2OC6H4)(SiMe2C5H4N) (624731-33-5) → (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene (865999-31-1) + Z-(Et)(C6H5)CC(4-Me2NCH2CH2OC6H4)(B(pin)) (624731-40-4)

Guidance literature:

E-(Et)(C₆H₅)CC(4-Me₂N(CH₂)2OC₆H₄)(SiMe₂C₅H₄N); With boron trichloride; In dichloromethane; at -41 ℃; for 5h;

2,3-dimethyl-2,3-butane diol; With triethylamine; In dichloromethane; at 20 ℃; for 3h;

With caesium carbonate; In dichloromethane; toluene; at 80 ℃; for 13h; Title compound not separated from byproducts;

DOI:10.1002/adsc.200404220

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) + boron trichloride (10294-34-5) + Z-(Et)(C6H5)CC(4-Me2N(CH2)2OC6H4)(SiMe2C5H4N) + E-(Et)(C6H5)CC(4-Me2N(CH2)2OC6H4)(SiMe2C5H4N) (624731-33-5) → (Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene (865999-31-1) + Z-(Et)(C6H5)CC(4-Me2NCH2CH2OC6H4)(B(pin)) (624731-40-4)

Guidance literature:

With caesium carbonate; In dichloromethane; toluene; alkenylsilane and BCl3 (2.2 equiv.) was employed; CH2Cl2, -40°C, 5 h; this mixt. treated with pinacol; treated with Cs2CO3 (10 equiv.) intoluene (80°C, 11 h);

DOI:10.1021/ja037566i

upstream raw materials:

2,3-dimethyl-2,3-butane diol

E-(Et)(C₆H₅)CC(4-Me₂N(CH₂)2OC₆H₄)(SiMe₂C₅H₄N)

1,1-bis(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-2-phenyl-1-butene

[2-(4-iodophenoxy)ethyl]dimethylamine

Downstream raw materials:

(E)-tamoxifen