5, 7-dihydroxy-2, 2-dimethyl-6-acetyl-chroman as well as synthesis method and application thereof
A synthetic method, dimethyl technology, applied in drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problem of not many synthetic methods, and achieve the effect of broad application prospects
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Embodiment 1
[0022] The synthetic method of 5,7-dihydroxy-2,2-dimethyl-6-acetyl-chroman:
[0023] Take 2,4,6-trihydroxyacetophenone (11.5 g, 60.0 mmol), add it to 460 mL of dry THF, add anhydrous K under stirring 2 CO 3 (16.6 g, 120 mmol), heated to reflux for 3 h, slowly added dropwise 1-bromo-3-methyl-2-butene (9.0 g, 60.0 mmol, one drop per ten seconds), stirred and heated to reflux for 6.5 h, then reduced pressure The solvent was evaporated, the residue was dissolved in water, extracted three times with 200 mL of ethyl acetate each time, the organic phases were combined, washed with an appropriate amount of water, saturated aqueous NaCl solution, and then washed with anhydrous Na 2 SO 4 Dry, add an appropriate amount of hydrochloric acid after drying, reflux under acid catalysis for 1.5h, evaporate the solvent under reduced pressure to obtain a crude product, which is separated and purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether=2 / 8 ) to give 5,7-...
Embodiment 2
[0027] The synthetic method of 5,7-dihydroxy-2,2-dimethyl-6-acetyl-chroman:
[0028] Take 2,4,6-trihydroxyacetophenone (23.0 g, 120.0 mmol), add it to 800 mL of dry THF, add anhydrous K under stirring 2 CO 3 (33.2 g, 240 mmol), heated to reflux for 9 h, slowly added dropwise 1-bromo-3-methyl-2-butene (18.0 g, 120.0 mmol, one drop per ten seconds), stirred and heated to reflux for 6 h, then reduced pressure The solvent was evaporated, the residue was dissolved in water, extracted three times with 400 mL of ethyl acetate each time, and the organic phases were combined, washed with an appropriate amount of water, saturated aqueous NaCl solution, and then washed with anhydrous Na 2 SO 4 Dry, add an appropriate amount of hydrochloric acid after drying, reflux under acid catalysis for 1.2 h, and evaporate the solvent under reduced pressure to obtain a crude product, which is separated and purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether=2 / 8 ) to...
Embodiment 3
[0032] 1.1 The synthetic method of 5,7-dihydroxy-2,2-dimethyl-6-acetyl-chroman:
[0033] Take 2,4,6-trihydroxyacetophenone (5.75 g, 30.0 mmol), add it to 200 mL of dry THF, add anhydrous K under stirring 2 CO 3 (8.30 g, 60 mmol), heated to reflux for 6 h, slowly added dropwise 1-bromo-3-methyl-2-butene (4.5 g, 30.0 mmol, one drop per ten seconds), stirred and heated to reflux for 6 h, dried An appropriate amount of hydrochloric acid was added, refluxed under acid catalysis for 1 h, the solvent was evaporated under reduced pressure, the residue was dissolved in water, extracted three times with 100 mL of ethyl acetate each time, and the organic phases were combined, washed with an appropriate amount of water and saturated aqueous NaCl solution, and then washed with anhydrous Na 2 SO 4Dry, evaporate the solvent under reduced pressure to obtain crude product, which is separated and purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 2 / 8) to ob...
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