5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde
• CAS No.: 230623-80-0
• Molecular Formula: C₄₆H₆₃NO₃SSi
• Molecular Weight: 738.163

Synonyms:

Chemical Property of 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde

Chemical Property:

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Technology Process of 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde

There total 14 articles about 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde 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:

4-Bromothiophen-2-aldehyde (18791-75-8) → 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde (230623-80-0)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / ethanol / 4 h / Ambient temperature

2: imidazole / CH₂Cl₂; dimethylformamide / 1.5 h / Ambient temperature

3: 42 percent / NiCl₂(dppp) / tetrahydrofuran / 24 h / -10 °C

4: 60 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature

5: conc. HCl / 4 h / Ambient temperature

6: xylene / Heating

7: 61 percent / EtONa / ethanol / 5 h / Heating

8: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C, 1 h; room temperature, 3 h

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tetrabutyl ammonium fluoride; sodium ethanolate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/jo981707v

Reference yield:

(4-bromothiophen-2-yl)methanol (79757-77-0) → 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde (230623-80-0)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole / CH₂Cl₂; dimethylformamide / 1.5 h / Ambient temperature

2: 42 percent / NiCl₂(dppp) / tetrahydrofuran / 24 h / -10 °C

3: 60 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature

4: conc. HCl / 4 h / Ambient temperature

5: xylene / Heating

6: 61 percent / EtONa / ethanol / 5 h / Heating

7: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C, 1 h; room temperature, 3 h

With 1H-imidazole; hydrogenchloride; n-butyllithium; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tetrabutyl ammonium fluoride; sodium ethanolate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/jo981707v

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-(2-{4-[(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-amino]-phenyl}-vinyl)-3-hexyl-thiophene-2-carbaldehyde (230623-80-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / imidazole / dimethylformamide; CH₂Cl₂ / 1.5 h / Ambient temperature

2: 94 percent / NBS / dimethylformamide / Ambient temperature

3: 1.) t-BuLi / 1.) THF, pentane, -78 deg C, 10 min, 2.) -78 deg C, 15 min; room temperature, 2 h

4: 61 percent / EtONa / ethanol / 5 h / Heating

5: 1.) n-BuLi / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C, 1 h; room temperature, 3 h

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; tert.-butyl lithium; sodium ethanolate; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo981707v

upstream raw materials:

N,N-dimethyl-formamide

(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-ethyl}-phenyl)-(4-butyl-phenyl)-{4-[2-(4-hexyl-thiophen-2-yl)-vinyl]-phenyl}-amine

4-Bromothiophen-2-aldehyde

(4-bromothiophen-2-yl)methanol

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