ethyl 5-hydroxy-2-(4-methoxyphenyl)benzofuran-3-carboxylate synthesis
- Product Name:ethyl 5-hydroxy-2-(4-methoxyphenyl)benzofuran-3-carboxylate
- CAS Number:5010-38-8
- Molecular formula:C18H16O5
- Molecular Weight:312.32
Yield:5010-38-8 84%
Reaction Conditions:
with anhydrous zinc chloride in dichloromethane at 110; for 0.5 h;Microwave irradiation;Sealed vessel;
Steps:
5.3. General protocol for synthesis of ethyl 5-hydroxy-2-arylbenzofuran-3-carboxylates (2)
General procedure: Appropriately substituted ethyl 3-aryl-3-oxopropionate (1 mol equiv), p-benzoquinone (1.1 mol equiv), anhydrous ZnCl2 (0.7 mol equiv) and 10 mL dichloromethane in a 20 mL microwavable sealed vial (with stand pressure up to 25 bars) were microwaved for 30 min at 110 °C in biotage initiator. Reaction was monitored by TLC (ethyl acetate/hexanes) and 1H NMR spectroscopy. The crystalline solid separated out in the vial was filtered, washed with dichloromethane and dried over vacuum to provide pure product. Furthermore crude left was recrystallized from ethyl acetate-hexane to provide the desired compound in overall good yield.
References:
Kumar, Satish;Namkung, Wan;Verkman;Sharma, Pawan K. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 14,p. 4237 - 4244] Location in patent:experimental part
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