Preparation method of thiophene compound with alcoholamine group in side chain
A technology of alcohol amine groups and compounds, which is applied in the field of synthesis of thiophene derivatives, can solve the problems of high raw material prices of halogenated glycols, difficulties in thiophene compounds, and low overall yield, and achieve high yield, easy availability of raw materials, and excellent reaction conditions mild effect
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Embodiment 1
[0020] The synthesis of embodiment 1 compound a
[0021] 1) Synthesis of 2-(2-(2-hydroxyethoxy) ethoxy) ethyl-4-tosylate, the reaction formula is as follows:
[0022]
[0023] The reaction process is: triethylene glycol (262.0mmol), triethylamine (40mmol) and dichloromethane (30mL) are mixed and placed in a 250mL three-necked flask; p-toluenesulfonyl chloride (26mmol) and dichloromethane (35mL ) was placed in a constant pressure dropping funnel and added dropwise to a three-neck flask. Stir in an ice-salt bath under the protection of a nitrogen balloon, and turn to room temperature when the ice is completely melted. The total reaction time is about 12 hours. The extent of the reaction was detected by thin layer chromatography (TLC). When TLC showed that the raw material spot in the reactant became lighter, the reaction was stopped. The reaction mixture was cooled to room temperature, washed three times with water, the aqueous phase was extracted with dichloromethane, and...
Embodiment 2
[0029] The synthesis of embodiment 2 compound b
[0030] 1) Synthesis of 2-(2-(2-(thiophen-3-yloxy)ethoxy)ethoxy)ethyl-4-toluenesulfonate, the reaction formula is as follows:
[0031]
[0032] The reaction process is: 3-methoxythiophene (5.0mmol), l2-(2-(2-hydroxyethoxy)ethoxy)ethyl-4-toluenesulfonate (8.0mmol), p-toluenesulfonate Add acid monohydrate (1.0 mmol) and 30 mL of toluene into a 250 mL three-necked flask, stir and heat to 100° C. under the protection of nitrogen balloon. During the reaction period, the reaction degree was detected by TLC method. After the reaction was completed, the solvent was evaporated to dryness with a rotary evaporator. Finally, it is purified by 100-200 mesh silica gel column chromatography. Petroleum ether: ethyl acetate = 4:3 (V / V) was used as the eluent. Finally, 1.20 g (3 mmol) of a yellow oily liquid product was obtained with a yield of 61%.
[0033] Product characterization data: FTIR (KBr, cm -1 ): υ3124, 2883, 1749, 1591, 1535, ...
Embodiment 3
[0038] The synthesis of embodiment 3 compound c
[0039] 1) Synthesis of 3-(2-(2-(2-(diethanolamine) ethoxy) ethoxy) ethoxy) thiophene, the reaction formula is as follows:
[0040]
[0041] The reaction process is: 2-(2-(2-(thiophen-3-yloxy)ethoxy)ethoxy)ethyl-4-toluenesulfonate (1.5mmol), diethanolamine (1.65mmol) , anhydrous sodium carbonate (1.8 mmol) and acetonitrile (30 mL) were added to a 250 mL three-necked flask, stirred under nitrogen balloon protection and heated to reflux. During the reaction, the degree of reaction was detected by TLC method. After the reaction was completed, the precipitate was removed by suction filtration, and the filtrate was evaporated to dryness with a rotary evaporator. Pour into 60 mL of dichloromethane, extract three times with water, add 30 mL of dichloromethane to the aqueous phase to extract the organic matter, then combine the organic phases with anhydrous MgSO 4 Dry, filter, and spin off the organic solvent. Finally, it is puri...
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