Synthesis method of mono-substituted ferrocene ramification containing 1,2,3-triazole heterocycle
A ferrocene derivative and heterocyclic single technology, which is used in liquid crystal materials, organic chemistry, metallocene, etc.
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Embodiment 1
[0041] Compound of Example 1 IIa Preparation of:
[0042]
[0043] In a 100 mL round bottom flask, take 4-azidophenol (0.135 g, 1 mmol) and dissolve it in 10 mL of anhydrous dichloromethane. Under the catalysis of DMAP (0.012 g, 0.1 mmol), 3,4,5-tridecyloxybenzoyl chloride ( 0.61 g, 1 mmol). After dropping, the reaction was carried out at room temperature for 1 h, and the reaction progress was monitored by TLC. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, and the eluent was petroleum ether and ethyl acetate (6:1, V:V). The first colorless product was collected, concentrated to obtain a transparent liquid, and recrystallized with absolute ethanol-dichloromethane to obtain a white powder 4-azidophenyl-3,4,5-tridecyloxybenzoate ( IIa ) 0.51 g, yield 72%, melting point 47 o C;
[0044] IR (KBr, ν, cm -1 ) 2927 (C-H), 2854 (C-H), 2114 (N 3 ), 1737 (C=O), 1586 (Ar-C), 1502 (Ar-C), 1189 (C-O); 1 H...
Embodiment 2
[0045] Compound of Example 2 IIb Preparation of:
[0046]
[0047] In a 100 mL round bottom flask, take 4-azidophenol (0.135 g, 1 mmol) and dissolve it in 10 mL of anhydrous dichloromethane. Under the catalysis of DMAP (0.012 g, 0.1 mmol), 3,4,5-tris(dodecyloxy) dissolved in 10 mL of anhydrous dichloromethane was slowly added dropwise to the round-bottomed flask with stirring in an ice-water bath. Benzoyl chloride (0.69 g, 1 mmol). After dropping, the reaction was carried out at room temperature for 1 h, and the reaction progress was monitored by TLC. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, and the eluent was petroleum ether and ethyl acetate (6:1, V:V). The first colorless product was collected, concentrated to obtain a transparent liquid, and recrystallized from absolute ethanol-dichloromethane to obtain a white powder 4-azidophenyl-3,4,5-tri(dodecyloxy)benzene Ester ( IIb ) 0.58 g, yiel...
Embodiment 3
[0049] Compound of Example 3 IIc Preparation of:
[0050]
[0051] In a 100 mL round bottom flask, take 4-azidophenol (0.135 g, 1 mmol) and dissolve it in 10 mL of anhydrous dichloromethane. Under the catalysis of DMAP (0.012 g, 0.1 mmol), 3,4,5-tris(tetradecyloxy) dissolved in 10 mL of anhydrous dichloromethane was slowly added dropwise to the round-bottomed flask with stirring in an ice-water bath. Benzoyl chloride (0.78 g, 1 mmol). After dropping, the reaction was carried out at room temperature for 1 h, and the reaction progress was monitored by TLC. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, and the eluent was petroleum ether and ethyl acetate (6:1, V:V). The first colorless product was collected, concentrated to obtain a transparent liquid, and recrystallized from absolute ethanol-dichloromethane to obtain a white powder 4-azidophenyl-3,4,5-tritetradecyloxy)benzene Ester ( IIc ) 0.61 g, ...
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