Acetic Acid → Methyl 2-iodo-3-methoxyprop-2-enoate

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]+.

1. additionwas added
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with dichloromethane
4. washThe combined organic extracts were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and water
5. dry with materialwere dried over anhydrous sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (PE:EA=1:5)

ORD record

ord-a0fc491348a341bfb9d9cd8e60591315

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079930B2