ethyl 5,8-bis(benzyloxy)-4-{[tert-butyl(dimethyl)silyl]oxy}naphthalene-2-carboxylate

Base Information

• Chemical Name: ethyl 5,8-bis(benzyloxy)-4-{[tert-butyl(dimethyl)silyl]oxy}naphthalene-2-carboxylate
• CAS No.: 500777-06-0
• Molecular Formula: C33H38O5Si
• Molecular Weight: 542.73700
• Mol file: 500777-06-0.mol

Synonyms:Pyrazinecarboxylic acid,5,6-dimethyl-,ethyl ester;

Chemical Property of ethyl 5,8-bis(benzyloxy)-4-{[tert-butyl(dimethyl)silyl]oxy}naphthalene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 629.547oC at 760 mmHg
• Flash Point: 277.826oC
• PSA: 53.99000
• Density: 1.108g/cm3
• LogP: 8.55850

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 5,8-bis(benzyloxy)-4-{[tert-butyl(dimethyl)silyl]oxy}naphthalene-2-carboxylate

There total 2 articles about ethyl 5,8-bis(benzyloxy)-4-{[tert-butyl(dimethyl)silyl]oxy}naphthalene-2-carboxylate 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5,8-bis-benzyloxy-4-hydroxy-naphthalene-2-carboxylic acid ethyl ester (500777-13-9) → ethyl 5,8-bisbenzyloxy-4-(tert-butyldimethylsilyloxy)-2-naphthoate (500777-06-0)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 25 ℃; for 2h;

DOI:10.1002/1099-0690(200210)2002:19<3341::AID-EJOC3341>3.0.CO;2-K

Reference yield:

4-acetoxy-5,8-bis-benzyloxy-naphthalene-2-carboxylic acid ethyl ester (500776-95-4) → ethyl 5,8-bisbenzyloxy-4-(tert-butyldimethylsilyloxy)-2-naphthoate (500777-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / EtONa / ethanol / 1 h / Heating

2: 97 percent / imidazole; DMAP / dimethylformamide / 2 h / 25 °C

With 1H-imidazole; dmap; sodium ethanolate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200210)2002:19<3341::AID-EJOC3341>3.0.CO;2-K

Reference yield: 98.0%

ethyl 5,8-bisbenzyloxy-4-(tert-butyldimethylsilyloxy)-2-naphthoate (500777-06-0) → [5,8-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)naphthalen-2-yl]methanol (500777-07-1)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.333333h;

DOI:10.1002/1099-0690(200210)2002:19<3341::AID-EJOC3341>3.0.CO;2-K

upstream raw materials:

tert-butyldimethylsilyl chloride

5,8-bis-benzyloxy-4-hydroxy-naphthalene-2-carboxylic acid ethyl ester

4-acetoxy-5,8-bis-benzyloxy-naphthalene-2-carboxylic acid ethyl ester

Downstream raw materials:

[5,8-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)naphthalen-2-yl]methanol

5,8-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-naphthalene-2-carbaldehyde

5,8-bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-naphthalene