pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester

Base Information

• Chemical Name: pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester
• CAS No.: 1259926-26-5
• Molecular Formula: C₂₁H₂₇NO₃S
• Molecular Weight: 373.516
• Mol file: 1259926-26-5.mol

Synonyms:pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester

Chemical Property of pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester

There total 6 articles about pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-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: 97.3%

pivalic acid 2-[(4-formyl-3-methoxyphenyl)-N-methylamino]ethyl ester (1259926-25-4) + [(thien-2-yl)methyl]triphenylphosphonium chloride (3462-99-5) → pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester (1259926-26-5)

Guidance literature:

With phenyllithium; In tetrahydrofuran; dibutyl ether; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/pola.24410

Reference yield:

pivalic acid 2-[(3-methoxyphenyl)-N-methylamino]ethyl ester (1259926-24-3) → pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester (1259926-26-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With phenyllithium; trichlorophosphate; In tetrahydrofuran; dibutyl ether; 2: Wittig reaction;

DOI:10.1002/pola.24410

Reference yield:

C8H9NO (1314931-05-9) → pivalic acid 2-{[3-methoxy-4-(2-thiophen-2-ylvinyl)phenyl]-N-methylamino}ethyl ester (1259926-26-5)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium tetrahydroborate / methanol / 2 h / Reflux

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

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

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

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

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

With pyridine; sodium tetrahydroborate; sodium hydrogencarbonate; phenyllithium; lithium bromide; trichlorophosphate; In tetrahydrofuran; methanol; dibutyl ether; toluene; acetonitrile; 6: Wittig reaction;

DOI:10.1002/pola.24410

upstream raw materials:

ethyl 2-[(3-methoxyphenyl)-N-methylamino]acetate

C₈H₉NO

pivalic acid 2-[(3-methoxyphenyl)-N-methylamino]ethyl ester

pivalic acid 2-[(4-formyl-3-methoxyphenyl)-N-methylamino]ethyl ester

Downstream raw materials:

2-{[3-methoxy-4-(2-thiophene-2-ylvinyl)phenyl]methylamino}ethanol

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

5-[2-(4-{[2-(tert-butylldimethylsilanyloxy)ethyl]methylamino}-2-methoxyphenyl)vinyl]thiophene-2-carbaldehyde

2-(tert-butyldimethylsiloxyethyl)[3-methoxy-4-(2-thiophen-2-yl-vinyl)phenyl]-N-methylamine

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.