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(2R)-1-(2,4-Difluorophenyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]-1-propanone, also known as Compound X, is an important intermediate in the production of various pharmaceuticals and agrochemicals.
The production process of Compound X involves several steps, including synthesis, purification, and characterization.
In this article, we will discuss the production process of Compound X in detail, highlighting the key steps and challenges involved in the process.
- Synthesis of (2R)-1-(2,4-Difluorophenyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]-1-propanone
The synthesis of Compound X involves several steps, including the condensation of 2,4-difluorophenyl mesylate with tetrahydro-2H-pyran-2-one, followed by the deprotection of the mesylate group and the addition of propanone.
The synthesis process can be represented by the following chemical equation:
Ph2CF2SO2CCH3 + H2C═O -> Ph2CF2C(O)CH3 + H2O
Ph2CF2C(O)CH3 + NaOH + H2O -> Ph2CF2C(OH)(Na) + CH3OH
Ph2CF2C(OH)(Na) + K2CO3 -> Ph2CF2C(O)K + NaHCO3
Ph2CF2C(O)K + H2O -> Ph2CF2C(OH)K + H3O+
Ph2CF2C(OH)K + NaNO3 -> Ph2CF2C(NO3)K + NaOH
Ph2CF2C(NO3)K + H2O -> Ph2CF2C(OH)K + KNO3
Ph2CF2C(OH)K -> (2R)-1-(2,4-Difluorophenyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]-1-propanone
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1.
Condensation of 2,4-difluorophenyl mesylate with tetrahydro-2H-pyran-2-one
The first step in the synthesis of Compound X is the condensation of 2,4-difluorophenyl mesylate with tetrahydro-2H-pyran-2-one.
The reaction is carried out in the presence of a solvent, such as dichloromethane or chloroform, and a base, such as triethylamine or sodium carbonate.
The condensation is performed at a temperature of around 0-10°C and takes several hours to complete.
1.
2.
Deprotection of the Mesylate Group
After the condensation reaction is complete, the mesylate group is deprotected using a strong acid, such as hydrochloric acid or sulfuric acid, in the presence of a solvent, such as ethyl acetate or toluene.
The deprotection reaction takes place at room temperature and is complete within a few hours.
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3.
Addition of Propanone
The deprotected compound is then treated with propanone in the presence of a catalyst, such as sodium hydroxide or potassium hydroxide, to form Compound X.
The reaction takes place at a temperature of around 80-100°C and is complete within a few hours.
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4.
Purification and Characterization of Compound X
After the synthesis of Compound X is complete, the product is purified using chromatography techniques, such as column chromatography or high-performance liquid chromatography (HPLC).
The purified compound is then characterized using various analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.
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Challenges in the Production Process
The production