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

Base Information

• Chemical Name: 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde
• CAS No.: 1061707-60-5
• Molecular Formula: C₂₃H₃₃NO₃SSi
• Molecular Weight: 431.671
• Mol file: 1061707-60-5.mol

Synonyms:5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-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: 70.0%

{5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-thiophen-3-yl}-methanol + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde (1061707-60-5)

Guidance literature:

{5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-thiophen-3-yl}-methanol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ja068322b

Reference yield:

4-Bromothiophen-2-aldehyde (18791-75-8) → 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde (1061707-60-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / NaBH₄; NaOH / methanol / 0 - 20 °C

2.1: 100 percent / conc. HCl / 2 h / 0 °C

3.1: 100 percent / 36 h / 90 °C

4.1: 90 percent / t-BuOK / tetrahydrofuran / 12 h

5.1: n-BuLi / hexane; diethyl ether / 0.42 h / -78 °C

5.2: 67 percent / hexane; tetrahydrofuran; diethyl ether / 0.17 h / -78 - 20 °C

6.1: NaBH₄; aq. NaOH / methanol; tetrahydrofuran / 1.5 h / 0 - 20 °C

7.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

7.2: 70 percent / hexane; tetrahydrofuran / -78 - 20 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; In tetrahydrofuran; methanol; diethyl ether; hexane;

DOI:10.1021/ja068322b

Reference yield:

diethyl (4-bromo-2-thienylmethyl)phosphonate (224958-14-9) → 5-[2-(4-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-phenyl)-vinyl]-3-hydroxymethyl-thiophene-2-carbaldehyde (1061707-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / t-BuOK / tetrahydrofuran / 12 h

2.1: n-BuLi / hexane; diethyl ether / 0.42 h / -78 °C

2.2: 67 percent / hexane; tetrahydrofuran; diethyl ether / 0.17 h / -78 - 20 °C

3.1: NaBH₄; aq. NaOH / methanol; tetrahydrofuran / 1.5 h / 0 - 20 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 70 percent / hexane; tetrahydrofuran / -78 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; In tetrahydrofuran; methanol; diethyl ether; hexane;

DOI:10.1021/ja068322b

upstream raw materials:

N,N-dimethyl-formamide

4-Bromothiophen-2-aldehyde

4-bromo-2-(chloromethyl)thiophene

diethyl (4-bromo-2-thienylmethyl)phosphonate