Methyl iodide → HCID 87132791, compound

NaH (washed with n-hexane in advance, 2.01 g, 76.24×1.1 mmol) was added to a dry THF (100 mL) solution of N-(3-ethoxypropyl)formamide (10.00 g, 76.24 mmol) under an argon atmosphere with ice-bath cooling, and stirred for 30 minutes. A dry THF (10 mL) solution of methyl iodide (5.7 mL, 76.24×1.2 mmol) was added dropwise to the reaction mixture under an argon atmosphere with ice-bath cooling, it was then stirred for 30 minutes, and further stirred at room temperature for 90 minutes. NaH (washed with n-hexane in advance, 0.20 g, 76.24×0.1 mmol) was again added and it was stirred at room temperature for 1 hour. After cooling with ice-bath, n-hexane (100 mL) was added to the reaction mixture and it was stirred for 1 hour, and insoluble materials were then removed by filtration with a pad of Celite. A residue obtained by concentrating the filtrate to dryness was purified by vacuum distillation (fraction at 0.6 kpa, 91° C. collected), and FEP (4.17 g, 28.68 mmol, 38%) was obtained as a pale yellow clear liquid.

1. temperaturecooling
2. temperaturecooling
3. stirringit was then stirred for 30 minutes
4. stirringfurther stirred at room temperature for 90 minutes
5. stirringit was stirred at room temperature for 1 hour
6. temperatureAfter cooling with ice-bath
7. stirringwas stirred for 1 hour
8. custominsoluble materials were then removed by filtration with a pad of Celite
9. customA residue obtained
10. concentrationby concentrating the filtrate to dryness
11. distillationwas purified by vacuum distillation (fraction at 0.6 kpa, 91° C. collected)
12. customFEP (4.17 g, 28.68 mmol, 38%) was obtained as a pale yellow clear liquid

ORD record

ord-83e75fc1d194417490cf45e59cc9e161

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067595B2