Acetic Acid → Methyl 2-iodo-3-methoxyprop-2-enoate
Reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH:4]=[CH:5][O:6][CH3:7].[I:9]N1C(=O)CCC1=O.C(O)(=O)C.C(N(CC)CC)C>O.ClCCl>[I:9][C:4](=[CH:5][O:6][CH3:7])[C:3]([O:2][CH3:1])=[O:8]Participants
7
[CH3:1][O:2][C:3](=[O:8])[CH:4]=[CH:5][O:6][CH3:7].[I:9]N1C(=O)CCC1=O.C(O)(=O)C.C(N(CC)CC)C>O.ClCCl>[I:9][C:4](=[CH:5][O:6][CH3:7])[C:3]([O:2][CH3:1])=[O:8]
A mixture of methyl-3-methoxypropenoate, 37-f, (13.92 g, 120 mmol), N-iodosuccinimid (32 g, 140 mmol), glacial acetic acid (18 mL, 240 mmol), and dichloromethane (150 mL) was stirred at room temperature for 24 h. Triethylamine (50 mL, 36 mmol) was added, and the reaction mixture was stirred at room temperature for 12 h before water was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and water, and were dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash chromatography (PE:EA=1:5) to afford compound, 37-g (30.5 g, crude). 1H NMR (300 MHz, CDCl3) δ 7.69 (s, 1H), 4.01 (s, 3H), 3.80 (s, 3H); LC-MS (ESI): 243 [M+H]+.
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