(E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol

Base Information

• Chemical Name: (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol
• CAS No.: 334866-08-9
• Molecular Formula: C₂₉H₂₉NO₂
• Molecular Weight: 423.555

Synonyms:(E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol

Chemical Property of (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol

Chemical Property:

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Technology Process of (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol

There total 2 articles about (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol 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-vinyl-benzaldehyde (1791-26-0) → (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol (334866-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 67 percent / potassium acetate; tetrapropylammonium bromide / palladium acetate / dimethylformamide / 2 h / 60 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 2 h / 0 °C

2.2: 62 percent / hexane; tetrahydrofuran / 0.75 h / -78 - 20 °C

With n-butyllithium; tetra-n-propylammonium bromide; potassium acetate; palladium diacetate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Heck reaction / 2.2: Wittig reaction;

DOI:10.1002/1521-3765(20010119)7:2<368::AID-CHEM368>3.0.CO;2-2

Reference yield:

N-Boc-2,5-diiodopyrrole (117657-44-0) → (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol (334866-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 67 percent / potassium acetate; tetrapropylammonium bromide / palladium acetate / dimethylformamide / 2 h / 60 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 2 h / 0 °C

2.2: 62 percent / hexane; tetrahydrofuran / 0.75 h / -78 - 20 °C

With n-butyllithium; tetra-n-propylammonium bromide; potassium acetate; palladium diacetate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Heck reaction / 2.2: Wittig reaction;

DOI:10.1002/1521-3765(20010119)7:2<368::AID-CHEM368>3.0.CO;2-2

Reference yield: 45.0%

2-[2-(4-iodo-phenyl)-vinyl]-pyrrole-1-carboxylic acid tert-butyl ester + (E,E)-2,5-Bis-[2'-(4''-vinylphenyl)-vinyl]-[1H]-N-tert-butyloxycarbonyl-pyrrol (334866-08-9) → 2,5-Bis-{(E)-2-[4-((E)-2-{4-[(E)-2-(1-tert-butoxycarbonyl-1H-pyrrol-2-yl)-vinyl]-phenyl}-vinyl)-phenyl]-vinyl}-pyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:

With tetra-n-propylammonium bromide; potassium acetate; palladium diacetate; at 80 ℃; for 3h;

DOI:10.1055/s-2001-11385

upstream raw materials:

4-vinyl-benzaldehyde

N-Boc-2,5-diiodopyrrole

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