1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene

Base Information

• Chemical Name: 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene
• CAS No.: 429686-76-0
• Molecular Formula: C₂₆H₃₄O₂Si₂
• Molecular Weight: 434.726

Synonyms:1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene

Chemical Property of 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene

Chemical Property:

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Technology Process of 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene

There total 8 articles about 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene 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:

1-bromo-4-(trimethylsilyl)-1,3-butadiyne (110373-04-1) + 1-buta-1,3-diynyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-benzene (429686-71-5) → 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene (429686-76-0) + 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-(8-trimethylsilanyl-octa-1,3,5,7-tetraynyl)-benzene + 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-dodeca-1,3,5,7,9,11-hexaynyl-benzene + 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-(12-trimethylsilanyl-dodeca-1,3,5,7,9,11-hexaynyl)-benzene

Guidance literature:

1-buta-1,3-diynyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-benzene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

With copper(l) chloride; In tetrahydrofuran; hexane; for 0.5h;

1-bromo-4-(trimethylsilyl)-1,3-butadiyne; With pyridine; In tetrahydrofuran; for 1.3h; Title compound not separated from byproducts;

DOI:10.1002/1521-3765(20020118)8:2<408::AID-CHEM408>3.0.CO;2-L

Reference yield:

3,5-dihydroxybenzaldehyde (26153-38-8) → 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene (429686-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / DMAP; Et₃N / dimethylformamide / 18 h / 20 °C

2: 97 percent / PPh₃ / CH₂Cl₂ / 0.17 h / 0 - 20 °C

3: 95 percent / LDA / hexane; tetrahydrofuran / -78 °C

4: 71 percent / TMEDA; CuCl; O₂ / acetone / 43 h / 20 °C

5: 95 percent / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h

With dmap; N,N,N,N,-tetramethylethylenediamine; oxygen; potassium carbonate; triethylamine; triphenylphosphine; copper(l) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 4: Hay reaction;

DOI:10.1002/1521-3765(20020118)8:2<408::AID-CHEM408>3.0.CO;2-L

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-octa-1,3,5,7-tetraynyl-benzene (429686-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / DMAP; Et₃N / dimethylformamide / 18 h / 20 °C

2: 97 percent / PPh₃ / CH₂Cl₂ / 0.17 h / 0 - 20 °C

3: 95 percent / LDA / hexane; tetrahydrofuran / -78 °C

4: 71 percent / TMEDA; CuCl; O₂ / acetone / 43 h / 20 °C

5: 95 percent / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h

With dmap; N,N,N,N,-tetramethylethylenediamine; oxygen; potassium carbonate; triethylamine; triphenylphosphine; copper(l) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 4: Hay reaction;

DOI:10.1002/1521-3765(20020118)8:2<408::AID-CHEM408>3.0.CO;2-L

upstream raw materials:

1-bromo-4-(trimethylsilyl)-1,3-butadiyne

1-buta-1,3-diynyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-benzene

3,5-dihydroxybenzaldehyde

tert-butyldimethylsilyl chloride

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