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CAS No. : | 7044-92-0 | MDL No. : | MFCD00719462 |
Formula : | C10H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AIBJDPZNCNFKMR-UHFFFAOYSA-N |
M.W : | 162.19 | Pubchem ID : | 595698 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Weigh 5g of raw materials (19mmol) and 0.17g, 0.95mmol of hexamethylphosphoric triamide (HMPA), put them into a 500mL three-necked flask with a built-in thermometer, and after 3 times of vacuum ventilation,Place it in a dry ice ethanol bath, control the temperature at -78C, add 2.1 equiv tert-butyl lithium (39.9 mmol, 30.69 mL, 1.3 M/L) dropwise, and the addition is completed in 1 hour. Slowly rise to room temperature, and continue stirring at room temperature for 20 min. Then the reaction system was reset in a dry ice ethanol bath, kept at -78C, and 13.89g of DMF was slowly added dropwise to the system. After the addition was completed, the dry ice ethanol bath was removed, and the mixture was stirred at room temperature for 50 minutes. Under ice bath, 40mL saturated aqueous ammonium chloride solution was added dropwise to the reaction system and quenched; ethyl acetate was extracted twice, the organic phase was washed twice with saturated brine, the organic phase was dried, concentrated under reduced pressure, evaporated to dryness, and the crude product was subjected to Purified by column chromatography, 2.54 g of white solid was obtained with a yield of 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With iodine; In acetonitrile; at 20℃; for 0.5h; | General procedure: A round-bottomed flask (10 mL) was charged with dialdehyde (1.0 mmol),5-hydroxyindole (0.53 g, 4 mmol), and iodine (0.05 g, 0.2 mmol) in MeCN (5 mL).This mixture was then stirred at room temperature for 0.5 to 8 h. The reactionmixture was treated with aqueous Na2S2O3, andthe solution was extracted with ethyl acetate (3 × 20 mL). The combined organiclayers were dried over MgSO4 and filtered. The solvent wasremoved under reduced pressure, and the residue was subjected to columnchromatography (ethyl acetate/hexane, 1/1), followed by recrystallization |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; In water; for 2h;Reflux; | Compound 8 (4.96 g 20 mmol) was refluxed in water(5 mL) and TFA (30 mL) for 2 h. The mixture was extracted with ethyl acetate, washed with Na2CO3 aqueous solution, dried over MgSO4, and evaporated under reduced pressure, giving the crude compound which was purified by flash chromatography with hexane/ethyl acetate (10:1) as eluent to afford the title compound as a light yellow solid. 1H NMR (400 MHz, CDCl3, 298K, TMS) δ10.30 (s, 2H), 7.65 (s, 2H), 2.66 (s, 6H). |