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Silica sources (TEOS and β-CD-organosilane product) were added dropwise to reaction mixture under continuous stirring at 293 K.
After the injection of 2 mL aqueous ammonia solution (25 wt%), tetraethyl orthosilicate (TEOS, 6.0 mL) was consecutively added to the mixture under continuous mechanical stirring.
Thermolysis of that mixture under continuous flow at 110 °C with concomitant aerial oxidation, gave the quinone 44, from which our target 43 was readily derived.
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The reaction mixture was put under continuous stirring for 22 h.
After that, dichloromethane (100 mL) was added and the mixture was neutralized, under continuous stirring at 0 °C, with sodium bicarbonate 10%.
The mixture was incubated at 30 °C under continuous shaking.
The mixture was heated to 70 °C under continuous stirring.
The mixture is refluxed at 70 °C under continuous stirring for 2 h.
The dried plant material (~500 g) was ground prior to solvent extraction with a mixture of MeOH CH2Cl2 (1:1; v/v) overnight under continuous agitation at 20 °C.
Such mixture was kept at room temperature under continuous stirring.
A Zn(NO3 2 solution (2.5 mL, 0.1 M) was then added to the solution, which was continually stirred for 5 min. Then NaOH solution (40 mL, 0.1 M) was directly added to the above solution dropwise, and the resulting mixture was maintained for 30 min under continuous stirring.
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