1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane

Base Information

• Chemical Name: 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane
• CAS No.: 307930-99-0
• Molecular Formula: C₄₈H₅₆N₂O₂Si₂
• Molecular Weight: 749.156

Synonyms:1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane

Chemical Property of 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane

Chemical Property:

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Technology Process of 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane

There total 7 articles about 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane 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:

tris-iso-propylsilyl acetylene (89343-06-6) → 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane (307930-99-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CuI; Et₃N / Pd(PPh₃)2Cl₂ / 13 h / 20 - 50 °C

2.1: 12.15 g / NaOH / ethanol; H₂O / 12 h / 20 °C

3.1: 85 percent / SOCl₂ / benzene / 36 h / Heating

4.1: EtMgBr / toluene; tetrahydrofuran / 0.08 h / 20 °C

4.2: 65 percent / toluene / 20 °C

With sodium hydroxide; copper(l) iodide; thionyl chloride; ethylmagnesium bromide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; water; toluene; benzene; 1.1: coupling / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Metallation / 4.2: Acylation;

DOI:10.1021/jo000882k

Reference yield:

4-iodobenzoic acid ethyl ester (51934-41-9) → 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane (307930-99-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CuI; Et₃N / Pd(PPh₃)2Cl₂ / 13 h / 20 - 50 °C

2.1: 12.15 g / NaOH / ethanol; H₂O / 12 h / 20 °C

3.1: 85 percent / SOCl₂ / benzene / 36 h / Heating

4.1: EtMgBr / toluene; tetrahydrofuran / 0.08 h / 20 °C

4.2: 65 percent / toluene / 20 °C

With sodium hydroxide; copper(l) iodide; thionyl chloride; ethylmagnesium bromide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; water; toluene; benzene; 1.1: coupling / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Metallation / 4.2: Acylation;

DOI:10.1021/jo000882k

Reference yield:

S-(2-pyridyl) 4-iodothiobenzoate (262267-33-4) → 1-{4-[2-(triisopropylsilyl)ethynyl]benzoyl}-5-mesityl-9-{4-[2-(trimethylsilyl)ethynyl]benzoyl}dipyrromethane (307930-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 percent / CuI; Et₃N; Ph₃P / Pd₂(dba)3 / tetrahydrofuran / 13 h / 20 - 50 °C

2.1: EtMgBr / tetrahydrofuran / 0.17 h / 20 °C

2.2: 84 percent / tetrahydrofuran / 0.5 h

3.1: EtMgBr / toluene; tetrahydrofuran / 0.08 h / 20 °C

3.2: 65 percent / toluene / 20 °C

With copper(l) iodide; ethylmagnesium bromide; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; toluene; 1.1: coupling / 2.1: Metallation / 2.2: Acylation / 3.1: Metallation / 3.2: Acylation;

DOI:10.1021/jo000882k

upstream raw materials:

4-iodobenzoic acid ethyl ester

tris-iso-propylsilyl acetylene

S-(2-pyridyl) 4-iodothiobenzoate

S-2-pyridyl 4-[2-(trimethylsilyl)ethynyl]benzothioate

Downstream raw materials:

{5-[{5-[hydroxy-(4-trimethylsilanylethynyl-phenyl)-methyl]-1H-pyrrol-2-yl}-(2,4,6-trimethyl-phenyl)-methyl]-1H-pyrrol-2-yl}-{4-[(triisopropylsilanyl)-ethynyl]-phenyl}-methanol

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