(E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one

Base Information

• Chemical Name: (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one
• CAS No.: 1424351-65-4
• Molecular Formula: C₂₁H₁₉FN₂O₄
• Molecular Weight: 382.391

Synonyms:(E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one

Chemical Property of (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one

Chemical Property:

Purity/Quality:

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Technology Process of (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one

There total 7 articles about (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one 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: 96.0%

1-[2-hydroxy-4,6-dimethoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]ethanone (1424351-63-2) + 4-fluorobenzaldehyde (459-57-4) → (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one (1424351-65-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 ℃; for 24h;

DOI:10.3109/14756366.2013.873037

Reference yield:

1,2,3-trimethoxybenzene (621-23-8) → (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one (1424351-65-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aluminum (III) chloride / diethyl ether / 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / acetone / 12 h / Reflux

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere

4.1: hydrazine hydrate / 0.5 h / 20 °C

5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

6.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / 20 °C / Inert atmosphere; Cooling with ice

7.1: sodium hydroxide / ethanol; water / 0.08 h

7.2: 24 h / 20 °C

With aluminum (III) chloride; boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; hydrazine hydrate; sodium hydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; 1.1: |Friedel-Crafts Acylation / 6.1: |Friedel-Crafts Acylation / 7.1: |Claisen-Schmidt Condensation / 7.2: |Claisen-Schmidt Condensation;

DOI:10.1016/j.bmcl.2012.12.094

Reference yield:

1-(2,4,6-trimethoxyphenyl)ethanone (832-58-6) → (E)-3-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(1-methyl-1H-pyrazol-5-yl)phenyl)prop-2-en-1-one (1424351-65-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 1 h / Inert atmosphere

2.1: hydrazine hydrate / 0.5 h / 20 °C

3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / 20 °C / Inert atmosphere; Cooling with ice

5.1: sodium hydroxide / ethanol; water / 0.08 h

5.2: 24 h / 20 °C

With boron trifluoride diethyl etherate; sodium hydride; hydrazine hydrate; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 4.1: |Friedel-Crafts Acylation / 5.1: |Claisen-Schmidt Condensation / 5.2: |Claisen-Schmidt Condensation;

DOI:10.1016/j.bmcl.2012.12.094

upstream raw materials:

1,2,3-trimethoxybenzene

2-hydroxy-4,6-dimethoxyacetophenone

1-[2-hydroxy-4,6-dimethoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]ethanone

4-fluorobenzaldehyde

Downstream raw materials:

C₂₁H₁₇FN₂O₄

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