benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester

Base Information

• Chemical Name: benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester
• CAS No.: 884864-15-7
• Molecular Formula: C₁₇H₂₃BO₄
• Molecular Weight: 302.178
• Mol file: 884864-15-7.mol

Synonyms:benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester

Chemical Property of benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester

There total 4 articles about benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl 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: 63.0%

3-butynyl benzoate (122471-85-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester (884864-15-7)

Guidance literature:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With triethylamine; tris(1-methylethyl)phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In cyclohexane; for 0.5h;

3-butynyl benzoate; In cyclohexane; at 20 ℃;

DOI:10.1021/ol0601850

Reference yield:

2,3-dimethyl-2,3-butane diol (76-09-5) → benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester (884864-15-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 12 h / 20 °C

2: (PCy₃)Ru(=CHPh){-CH(N(2,4,6-Me₃Ph)CH₂CH₂N(2,4,6-Me₃Ph))}Cl₂ / CH₂Cl₂ / 12 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In diethyl ether; dichloromethane; 2: olefin cross-metathesis;

DOI:10.1021/jo0345345

Reference yield:

3-butenyl benzoate (18203-32-2) + 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane (72824-04-5,83947-58-4,83947-59-5,72824-05-6) → benzoic acid (Z)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester (884864-15-7) + benzoic acid (E)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl ester (581802-27-9)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 12h; Title compound not separated from byproducts; Heating;

DOI:10.1021/jo0345345

upstream raw materials:

3-butenyl benzoate

4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane

pinacol vinylboronate

3-butynyl benzoate

Downstream raw materials:

(E)-4-benzoyloxy-1-iodo-1-butene

Refernces

• 1、 Morrill, Christie,Grubbs, Robert H.. "Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides". . p. 6031 - 6034. Retrieved 2007/10/03.