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Method for synthesizing second-level trifluoromethyl propargyl alcohol
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A technology of trifluoromethyl propargyl alcohol and synthesis method, which is applied in the field of synthesis of fluorine-containing organic compounds, and achieves the effect of good chemical stability
Inactive Publication Date: 2017-06-27
HEFEI UNIV OF TECH
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[0005] The above-mentioned method of synthesizing trifluoromethyl propargyl alcohol has great limitation, they can only be used for the synthesis of three-level trifluoromethyl propargyl alcohol derivatives, and for the synthesis of the secondary propargyl alcohol of trifluoromethyl substitution but can't do anything
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Embodiment 1
[0041] This example synthesizes secondary trifluoromethyl propargyl alcohol 1,1,1-trifluoro-4-triisopropylsilyl-3-butyn-2-ol according to the following steps:
[0042] a. Preparation of 1-(hydroxyl)-1,2-phenyliodide-3(1H)-ketone
[0043]Add 2-iodobenzoic acid (8.00g, 32.2mmol) and sodiumperiodate (7.24g, 33.8mmol) in a dry 250mL flask equipped with a magnetic stirring bar, and then add 30vt% (volume percent) acetic acidaqueous solution ( 48mL). Fix the flask in an oil bath, connect the condensate return line and turn on the condensate. Heat the oil bath to 120°C and reflux for 4 hours; remove the oil bath and reflux tube after the reaction, add 180 mL of ice-water mixture (0°C) to the flask under dark conditions, cool to room temperature, and After standing for 1 h, it was filtered, washed with water (3*20 mL) and acetone (3*20 mL) successively, and dried to obtain 8.3 g of white crystals with a yield of 98%.
[0056] This example synthesizes secondary trifluoromethyl propargyl alcohol 1,1,1-trifluoro-4-phenyl-3-butyn-2-ol according to the following steps:
[0057] a. Preparation of 1-(hydroxyl)-1,2-phenyliodide-3(1H)-ketone
[0058] b, preparation of trimethylsilyl (phenyl) acetylene
[0059] in N 2 Under protection, trimethylsilylacetylene (4.2mL, 30mmol) and THF (48mL) were added to a dry 100mL flask equipped with a magnetic stir bar, then n-butyllithium (12mL) was added at -78°C and stirred 15min, then added iodobenzene (6.73g, 33mmol) and stirred for 5min, warmed up to room temperature and stirred for 6h; after the reaction was completed, NH 4 Cl saturated solution (40mL), then CH 2 Cl 2 (2*60mL) extraction, the organic phase was extracted with water, washed with brine, dried, filtered, concentrated, and separated by column chromatography (petroleumether as the eluent) to obtain 3.65 g of a colorless liquid with a yield of 70%.
[0060] c. Preparation of 1-[(phenyl)eth...
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technical field [0001] The invention relates to a method for synthesizing fluorine-containing organic compounds, in particular to a method for synthesizing secondary trifluoromethylpropargylalcohol. Background technique [0002] The introduction of fluorine-containing functional groups into organic molecules can significantly change the physical, chemical and biological properties of molecules. For example, fluorine-containing functional groups have the characteristics of strong electron-withdrawing induction effect, hydrophobic effect, and stable C-F bond. The introduction of fluorine-containing functional groups into organic molecules will significantly change the molecular dipole moment, acidity, lipophilicity, chemical and metabolic stability, etc. . The synthesis of fluorine-containing functional organic molecules and their applications in the fields of energy, materials, and medicine have become important contents of organic chemistry research. Among them, trifluor...
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