2-Propenoicacid,3-iodo,methylester,(Z)-
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2-Propenoicacid,3-iodo,methylester,(Z)-
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CAS No:
6214-23-9
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Formula:
C4H5IO2
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Chemical Name:
2-Propenoicacid,3-iodo,methylester,(Z)-
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Synonyms:
methyl 3-iodoprop-2-enoate;methyl (Z)-3-iodoprop-2-enoate;methyl 3-iodoacrylate;Methyl (Z)-3-Iodoacrylate;CTK5B4401;CTK8J6768;KS-00000GJS;89033-13-6;ANW-73546;MFCD09265518
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CAS No:
2-Propenoicacid,3-iodo,methylester,(Z)- Use and Manufacturing
15g (178mmol) Methyl propiolate and 26.3g (196mmol) Lithium iodide are dissolved in 178 mL of acetic acid, stir at 70 ° C for 11 h and add the 900 mL of water with stirring for quench the reaction, the reaction solution is neutralized with K2C03 until there is no C02 gas generated. Extracted three times with ether, and the combined organic phases were washed three times with saturated brine, dried over anhydrous sodium sulfate, after that filter, the filtrate has been concentrated and the resulting residue was purified by column chromatography (petroleum ether: ethyl acetate = 30: 1), than we get 32.4g light yellow oily liquid of (Z) -3-iodo-2-methyl acrylate (4), yield 89percentA mixture of methyl propiolate (15.0 g, 178 mmol) and LiI (26.3 g, 196 mmol) in acetic acid (178 mL) was stirred and heated at 70. The reaction was monitored by GC-Ms (after neutralization). After 11 h, water (900 mL) was added and neutralized with solid K2CO3 until no CO2 was evolved and then extracted with ether (1.8 L x 3). The extracts were dried over anhydrous Na2SO4 andconcentrated in vacuo to afford a crude oil, which was purified by silica gel column chromatography (PE/EA = 30/1) to afford(Z)-methyl 3-iodoacrylate 7 (32.36 g, 89percent) as a pale yellow oil.The synthesis of the polyene chains of different lengths began with the treatment of methyl propiolate 11 with sodium iodide in acetic acid(23, 24) to provide Z-iodoacrylate 12 in 58percent yield and 100 percent stereoselectivity.
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