CIS-3-IODOACRYLIC ACID ETHYL ESTER synthesis
- Product Name:CIS-3-IODOACRYLIC ACID ETHYL ESTER
- CAS Number:31930-36-6
- Molecular formula:C5H7IO2
- Molecular Weight:226.01
623-47-2
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31930-36-6
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Yield: 100%
Reaction Conditions:
with acetic acid;sodium iodide at 70; for 16 h;Inert atmosphere;
Steps:
8 Ethyl cis-3-iodoacrylate
A solution of ethyl propiolate (1.0 mL, 9.8 mmol) in glacial acetic acid (5 mL) was treated with sodium iodide (1.5 g, 10 mmol) and the reaction mixture was warmed up to 70 °C and stirred for 16 h.
The reaction was quenched with H2O (5 mL) followed by aq. NaOH (1 N, 5 mL) and extracted with diethyl ether (3 * 5 mL).
The combined organic phases were dried over Na2SO4, filtered and concentrated under vacuum to afford the desired iodoacrylate as orange oil in a quantitative yield (2.23 g, 9.8 mmol).
The product was used without any further purification. Rf 0.59 (Et2O/PE, 2.5:7.5); 1H NMR (500 MHz, CDCl3): δ 7.31 (1H, dd, J = 8.8, 1.0 Hz), 6.74 (1H, dd, J = 8.9, 1.3 Hz), 4.06 (2H, qd, J = 7.2, 1.7 Hz), 1.14 (3H, td, J = 7.2, 1.6 Hz); 13C NMR (125 MHz, CDCl3): δ 164.0, 129.6, 94.7, 60.4, 13.9; νmax (film) 1721, 1597, 1321, 1192, 1159, 1024 and 804 cm-1; HRMS (ESI) calcd for C5H7IO2 [M]+: 225.9491. Found: 225.9494.
References:
Pasqua, Adele E.;Ferrari, Frank D.;Crawford, James J.;Whittingham, William G.;Marquez, Rodolfo [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 5,p. 1062 - 1068]
64-17-5
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6214-35-3
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$79.00/250mg
31930-36-6
64 suppliers
$48.39/1g
16205-84-8
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$41.00/5g
31930-36-6
64 suppliers
$48.39/1g
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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