(E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1414125-76-0
• Molecular Formula: C₁₈H₂₇BO₆
• Molecular Weight: 350.22
• Mol file: 1414125-76-0.mol

Synonyms:(E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 78.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + (E)-4-(2-iodovinyl)-1,2-bis(methoxymethoxy)benzene (1414125-62-4) → (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1414125-76-0)

Guidance literature:

(E)-4-(2-iodovinyl)-1,2-bis(methoxymethoxy)benzene; With tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1055/s-0032-1316765

Reference yield:

3,4-bis-methoxymethoxy-benzaldehyde (6515-06-6) → (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1414125-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chromium dichloride / tetrahydrofuran; 1,4-dioxane / 0.08 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C

With chromium dichloride; tert.-butyl lithium; In tetrahydrofuran; 1,4-dioxane; hexane; 1.1: |Takai-Utimoto Olefination;

DOI:10.1055/s-0032-1316765

Reference yield: 65.0%

(E)-4-(3,7-dimethylocta-2,6-dienyl)-3,5-bis(methoxymethoxy)phenyl trifluoromethanesulfonate (1414124-79-0) + (E)-2-[3,4-bis(methoxymethoxy)styryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1414125-76-0) → 5-[(E)-3,4-bis(methoxymethoxy)styryl]-2-[(E)-3,7-dimethylocta-2,6-dienyl]-1,3-bis(methoxymethoxy)benzene (848190-46-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 90 ℃; for 8h; Inert atmosphere;

DOI:10.1055/s-0032-1316765

upstream raw materials:

3,4-bis-methoxymethoxy-benzaldehyde

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(E)-4-(2-iodovinyl)-1,2-bis(methoxymethoxy)benzene

Downstream raw materials:

5-[(E)-3,4-bis(methoxymethoxy)styryl]-2-[(E)-3,7-dimethylocta-2,6-dienyl]-1,3-bis(methoxymethoxy)benzene