A method for synthesizing benzothieno[3,2-b]chromones through ionic liquid-promoted intramolecular cross dehydrogenation coupling
A technology of chromone compounds and ionic liquids, applied in the direction of organic chemistry, can solve the problems of insufficient greenness and poor atom economy, and achieve the effect of simple operation, simple and mild conditions, and high reaction atom economy
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Embodiment 1
[0027] 11 H -Benzo[4,5]thieno[3,2- b ] Synthesis of chromone
[0028]
[0029] Add the ionic liquid accelerator [Bmim]Br (0.1 mmol), 3-phenoxybenzothiophene-2-aldehyde (0.2 mmol) into the reaction tube, then add TBHP (0.2 mL) and water (0.05 mL) sequentially, at 100 oMagnetically stir the reaction at C for 24 hours, cool to room temperature after the reaction, add 2 mL of water, then extract with ethyl acetate (3 × 10 mL), combine the organic phases and dry with anhydrous sodium sulfate, filter, and remove under reduced pressure Ethyl acetate, product 1 was obtained by column chromatography (eluent polarity: petroleum ether / ethyl acetate 8: 1). Yield: 82%.
Embodiment 2
[0031] 11 H -Benzo[4,5]thieno[3,2- b ] Gram-level synthesis of chromone
[0032]
[0033] Add the ionic liquid accelerator [Bmim]Br (4 mmol), 3-aryloxybenzothiophene-2-aldehyde (8 mmol) into the reaction tube, then add TBHP (8 mL) and water (2 mL) in sequence, in 100 o The reaction was carried out under magnetic stirring at C for 24 hours, cooled to room temperature after the reaction, and the obtained solid was filtered with suction, and the crude product was separated by column chromatography to obtain product 1 (eluent polarity: petroleum ether / ethyl acetate 8 : 1). Yield: 80%.
Embodiment 3
[0035] 2-fluoro-11 H -Benzo[4,5]thieno[3,2- b ] Synthesis of chromone
[0036]
[0037] Add the ionic liquid promoter [Bmim]Br (0.1 mmol), 3-(4-fluorophenoxy)benzothiophene-2-aldehyde (0.2 mmol) into the reaction tube, then add TBHP (0.2 mL) and water in sequence (0.05 mL), at 100 o Magnetically stir the reaction at C for 24 hours, cool to room temperature after the reaction, add 2 mL of water, then extract with ethyl acetate (3 × 10 mL), combine the organic phases and dry with anhydrous sodium sulfate, filter, and remove under reduced pressure Ethyl acetate, product 2 was obtained by column chromatography (eluent polarity: petroleum ether / ethyl acetate 12:1). Yield: 77%; 1 H NMR (400 MHz, CDCl 3 ): δ 8.20 (d, J =8.0 Hz,1H), 8.03 (dd, J = 8.4, 3.2 Hz, 1 H), 7.93 (d, J = 8.4 Hz, 1 H), 7.70(dd, J = 9.2, 4.0 Hz, 1 H), 7.65-7.61 (m, 1 H), 7.56 (td, J = 7.2, 0.8 Hz,1H), 7.50 (ddd, J = 9.2, 7.6, 3.2 Hz, 1 H). 13 C NMR (100 MHz, CDCl 3 ): δ 172.6(d, J CF = 2.2...
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