2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester

Base Information

• Chemical Name: 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester
• CAS No.: 1259926-34-5
• Molecular Formula: C₂₇H₃₁NO₃S
• Molecular Weight: 449.614
• Mol file: 1259926-34-5.mol

Synonyms:2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester

Chemical Property of 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester

There total 7 articles about 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl 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: 84.5%

2,2-dimethylpropionic acid 2-[(3-benzyloxy-4-formylphenyl)methylamino]ethyl ester (1259926-33-4) + [(thien-2-yl)methyl]triphenylphosphonium chloride (3462-99-5) → 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester (1259926-34-5)

Guidance literature:

[(thien-2-yl)methyl]triphenylphosphonium chloride; With phenyllithium; In tetrahydrofuran; dibutyl ether; for 0.333333h; Cooling with ice;

2,2-dimethylpropionic acid 2-[(3-benzyloxy-4-formylphenyl)methylamino]ethyl ester; In tetrahydrofuran; dibutyl ether; for 2h;

Reference yield:

3-(benzyloxy)-N-methylaniline (33905-38-3) → 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester (1259926-34-5)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate / acetonitrile / 4 h / Inert atmosphere; Reflux

2: sodium tetrahydroborate; lithium bromide / tetrahydrofuran / 5 h / Reflux; Inert atmosphere

3: pyridine / toluene / 4 h / 20 - 85 °C / Inert atmosphere

4: trichlorophosphate / 0 - 20 °C / Inert atmosphere

5: phenyllithium / tetrahydrofuran; dibutyl ether / 1.5 h / 0 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; sodium hydrogencarbonate; phenyllithium; lithium bromide; trichlorophosphate; In tetrahydrofuran; dibutyl ether; toluene; acetonitrile; 5: Wittig reaction;

DOI:10.1002/pola.24410

Reference yield:

2-[(3-benzyloxyphenyl)methylamino]ethanol (33905-39-4) → 2,2-dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester (1259926-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / toluene / 4 h / 20 - 85 °C / Inert atmosphere

2: trichlorophosphate / 0 - 20 °C / Inert atmosphere

3: phenyllithium / tetrahydrofuran; dibutyl ether / 1.5 h / 0 °C / Inert atmosphere

With pyridine; phenyllithium; trichlorophosphate; In tetrahydrofuran; dibutyl ether; toluene; 3: Wittig reaction;

DOI:10.1002/pola.24410

upstream raw materials:

o-(benzyloxy)aniline

2,2-dimethylpropionic acid 2-[(3-benzyloxyphenyl)methylamino]ethyl ester

2,2-dimethylpropionic acid 2-[(3-benzyloxy-4-formylphenyl)methylamino]ethyl ester

[(thien-2-yl)methyl]triphenylphosphonium chloride

Downstream raw materials:

[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]-[2-(tert-butyldimethylsilanyloxy)ethyl]methylamine

5-[2-(2-benzyloxy-4-{[2-(tert-butyldimethylsilanyloxy)-ethyl]methylamino}phenyl)vinyl]thiophene-2-carbaldehyde

5-(2-{2-benzyloxy-4-[(2-hydroxyethyl)-methylamino]-phenyl}-vinyl)-thiophene-2-carbaldehyde

2-(4-{2-[5-(2-{2-benzyloxy-4-[(2-hydroxyethyl)methylamino]phenyl}vinyl)thiophene-2-yl]vinyl}-3-cyano-5-phenyl-5-trifluoromethyl-5H-furan-2-ylidene)malononitrile

Refernces

• 1、 Piao, Xianqing,Zhang, Xianmin,Mori, Yuichi,Koishi, Masayuki,Nakaya, Akinari,Inoue, Shinichiro,Aoki, Isao,Otomo, Akira,Yokoyama, Shiyoshi. "Nonlinear optical side-chain polymers post-functionalized with high-β chromophores exhibiting large electro-optic property". . p. 47 - 54. Retrieved 2011/10/02.