Methyl 2-vinylnicotinate synthesis
- Product Name:Methyl 2-vinylnicotinate
- CAS Number:103441-72-1
- Molecular formula:C9H9NO2
- Molecular Weight:163.17
379670-43-6
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103441-72-1
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Yield: 84%
Reaction Conditions:
with hydrogen;palladium in ethyl acetate at 20; for 4 h;
Steps:
1.14 Methyl 2-vinylnicotinate
To a solution of methyl 2-ethynylnicotinate (0.43 g, 2.68 mmol, 1 eq) in EtOAc (12.0 mL), Pd Lindlar (0.13 g) was added.
Then the reaction was equipped with a balloon of hydrogen and stirred at room temperature.
After 4 h, the reaction mixture was filtered through a pad of Celite washing with EtOAc.
The filtrate was evaporated and the residue (as a brown oil) was used as such for the next step. (0.37 g, 84%).
1H NMR (300 MHz, CDCl3) δ 8.68 (dd, J = 4.6/1.8 Hz, 1-H), 8.14 (dd, J = 7.9/1.8 Hz, 1-H), 7.60 (dd, J = 16.8/10.7 Hz, 1-H), 7.21 (dd, J = 7.6/4.6 Hz, 1-H), 6.48 (dd, J = 16.8/2.2 Hz, 1-H), 5.58 (dd, J = 10.7/2.2 Hz, 1-H), 3.93 (s, 3-H); 13C NMR (75 MHz, CDCl3) δ 167.0, 155.1, 138.5, 133.9, 134.0, 132.1, 124.3, 122.0, 121.7, 52.5; GC-MS m/z 163 (M)+; IR (KBr) 2952, 1724, 1559, 1431, 1264, 1078 cm-1.
References:
Galli, Ubaldina;Mesenzani, Ornella;Coppo, Camilla;Sorba, Giovanni;Canonico, Pier Luigi;Tron, Gian Cesare;Genazzani, Armando A. [European Journal of Medicinal Chemistry,2012,vol. 55,p. 58 - 66,9]
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103441-72-1
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75927-49-0
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103441-72-1
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103441-72-1
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40134-18-7
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$6.00/5g
103441-72-1
22 suppliers
$438.31/1g