4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate

Base Information

• Chemical Name: 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate
• CAS No.: 1383545-61-6
• Molecular Formula: C₂₈H₂₆O₁₁
• Molecular Weight: 538.508

Synonyms:4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate

Chemical Property of 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate

Chemical Property:

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Technology Process of 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate

There total 2 articles about 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate 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: 94.0%

acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester (143631-95-2) + 1,1-dimethyl-2-propenyl isobutyl carbonate (164513-96-6) → 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate (1383545-61-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at -20 - 0 ℃; Inert atmosphere;

DOI:10.1055/s-0031-1290756

Reference yield:

quercetol (117-39-5,74893-81-5) → 4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate (1383545-61-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 130 - 140 °C / Inert atmosphere

2: 1H-imidazole; thiophenol / 1-methyl-pyrrolidin-2-one / 0 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / -20 - 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thiophenol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one;

DOI:10.1055/s-0031-1290756

Reference yield: 94.0%

4-[3,5-diacetoxy-7-(2-methylbut-3-en-2-yloxy)-4-oxo-4H-chromen-2-yl]-1,2-phenylene diacetate (1383545-61-6) + acetic anhydride (108-24-7) → 2-(3,4-diacetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-4H-chromene-3,5,7-triyl triacetate (1383545-66-1)

Guidance literature:

at 120 - 130 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0031-1290756

upstream raw materials:

acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester

1,1-dimethyl-2-propenyl isobutyl carbonate

quercetol

Downstream raw materials:

8-Prenylquercetin

2-(3,4-diacetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-4H-chromene-3,5,7-triyl triacetate

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