ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate

Base Information

• Chemical Name: ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate
• CAS No.: 1542756-25-1
• Molecular Formula: C₃₁H₃₃NO₄
• Molecular Weight: 483.607
• Mol file: 1542756-25-1.mol

Synonyms:ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate

Chemical Property of ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate

There total 9 articles about ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate 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%

ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-ol-4-oxy) acetate (1542755-96-3) + (2-chloroethyl)dimethylamine hydrochloride (4584-46-7) → ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate (1542756-25-1)

Guidance literature:

ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-ol-4-oxy) acetate; With potassium carbonate; In acetone; for 1h; Inert atmosphere; Sealed tube; Reflux;

(2-chloroethyl)dimethylamine hydrochloride; In acetone; Inert atmosphere; Sealed tube; Reflux;

DOI:10.1016/j.bmc.2013.10.051

Reference yield:

β-naphthaldehyde (66-99-9) → ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate (1542756-25-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: magnesium; iodine / tetrahydrofuran / 6.17 h / Sealed tube; Inert atmosphere; Reflux

1.2: 20 °C / Sealed tube; Inert atmosphere

2.1: trifluoroacetic acid; triethylsilane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 20 °C

4.1: tetra-n-butylammonium tribromide / chloroform / 20 °C

5.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

5.2: 20 °C

6.1: sodium carbonate; tris-(o-tolyl)phosphine; dichlorobis(tri-O-tolylphosphine)palladium / dichloromethane; water / 0.5 h / 80 °C / Inert atmosphere; Sealed tube

6.2: 20 - 80 °C / Inert atmosphere; Sealed tube

7.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Sealed tube; Reflux

7.2: Inert atmosphere; Sealed tube; Reflux

With triethylsilane; dichlorobis(tri-O-tolylphosphine)palladium; tetra-n-butylammonium tribromide; iodine; boron tribromide; sodium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; magnesium; tris-(o-tolyl)phosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; water; acetone; 6.1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2013.10.051

Reference yield:

(2-methoxyphenyl)(naphthalen-2-yl)methanol → ethyl 2-(1,1'-biphenyl-3-(naphthalen-2-yl)methyl-4'-[2-(dimethylamino)ethoxy]-4-oxy) acetate (1542756-25-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trifluoroacetic acid; triethylsilane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 20 °C

3.1: tetra-n-butylammonium tribromide / chloroform / 20 °C

4.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

4.2: 20 °C

5.1: sodium carbonate; tris-(o-tolyl)phosphine; dichlorobis(tri-O-tolylphosphine)palladium / dichloromethane; water / 0.5 h / 80 °C / Inert atmosphere; Sealed tube

5.2: 20 - 80 °C / Inert atmosphere; Sealed tube

6.1: potassium carbonate / acetone / 1 h / Inert atmosphere; Sealed tube; Reflux

6.2: Inert atmosphere; Sealed tube; Reflux

With triethylsilane; dichlorobis(tri-O-tolylphosphine)palladium; tetra-n-butylammonium tribromide; boron tribromide; sodium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; tris-(o-tolyl)phosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; water; acetone; 5.1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2013.10.051

upstream raw materials:

β-naphthaldehyde

4-bromo-phenol

ethyl 2-(4-bromo-2-((naphthalen-2-yl)methyl) phenoxy)acetate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol