ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate

Base Information

• Chemical Name: ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate
• CAS No.: 1593270-23-5
• Molecular Formula: C₁₇H₂₃BO₄
• Molecular Weight: 302.178
• Mol file: 1593270-23-5.mol

Synonyms:ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate

Chemical Property of ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate

There total 4 articles about ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate 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: 95.0%

phenylpropynoic acid ethyl ester (2216-94-6) + bis(pinacol)diborane (73183-34-3) → ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate (1593270-23-5)

Guidance literature:

With picoline; copper(ll) sulfate pentahydrate; water; at 20 ℃; for 4h; stereoselective reaction;

DOI:10.1055/s-0034-1380524

Reference yield:

phenylpropynoic acid ethyl ester (2216-94-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate (1593270-23-5) + (E)-ethyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

Guidance literature:

With tricyclohexylphosphine; In tetrahydrofuran; at 60 ℃; for 4h; Overall yield = 87 %Spectr.; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.8b00390

Reference yield:

benzaldehyde (100-52-7) → ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate (1593270-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C

1.2: 0 - 20 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -78 °C

2.2: -78 - 20 °C

3.1: picoline; copper(ll) sulfate pentahydrate / 12 h / 20 °C

With picoline; n-butyllithium; copper(ll) sulfate pentahydrate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/acs.orglett.9b00994

upstream raw materials:

phenylpropynoic acid ethyl ester

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

benzaldehyde

Downstream raw materials:

ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

4-phenylcoumarin