Isoflavone synthesis
- Product Name:Isoflavone
- CAS Number:574-12-9
- Molecular formula:C15H10O2
- Molecular Weight:222.24
Yield:574-12-9 88%
Reaction Conditions:
Stage #1: α-bromoacetophenonewith thiamine hydrochloride in ethanol at 20; for 0.25 h;Green chemistry;
Stage #2: salicylaldehyde in ethanol at 20; for 1 h;Green chemistry;Solvent;Time;Reagent/catalyst;
Steps:
Experimental
General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95% ethanol (water : 95% ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 °C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol %) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.
References:
Mishra, Priya;Singh, Sarita;Ankit, Preyas;Fatma, Shahin;Singh, Divya;Singh, Jagdamba [Bulletin of the Korean Chemical Society,2013,vol. 34,# 4,p. 1070 - 1076]
122775-34-2
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