2-Propenoicacid,3-(4-hydroxy-3-methoxyphenyl)-,2-phenylethylester,(E)- synthesis
- Product Name:2-Propenoicacid,3-(4-hydroxy-3-methoxyphenyl)-,2-phenylethylester,(E)-
- CAS Number:132335-98-9
- Molecular formula:C18H18O4
- Molecular Weight:298.33
Yield:132335-98-9 78%
Reaction Conditions:
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acidwith N,N,N,N,N,N-hexamethylphosphoric triamide;sodium carbonate for 0.5 h;
Stage #2: 1-phenyl-2-bromoethanewith potassium iodide at 20; for 48 h;
Steps:
General esterification method A (compounds 3-15, 26-27,34, 35, 42,43).
General procedure: To a stirredsolution of the acid (1 mmol) in dry hexamethyl phosphoramide (5 mL), Νa2CO3 (126 mg, 1.19 mmol) wasadded and stirring continued for 30 min. At the end of this period, thecorresponding bromide (1.14 mmol) was added to the reaction mixture followed bya catalytic amount of potassium iodide. The mixture was stirred at room temperaturefor 48 h, after which EtOAc (30 ml) and HCl 0.5 N (5 mL) were added. Theorganic phase was washed with brine, dried over Na2SO4,filtered and concentrated under reduced pressure. The crude product waspurified by column chromatography.
References:
Pagoni, Aikaterini;Daliani, Theohari;Macegoniuk, Katarzyna;Vassiliou, Stamatia;Berlicki, ?ukasz [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 9,p. 1085 - 1089] Location in patent:supporting information
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