Chloromethyl Methyl Ether → HCID 22292751, compound

A THF solution (15 mL) of 2-isopropylamino-1-propanol (1.23 g, 10.5 mmol) was added dropwise to a suspension of sodium hydride (504 mg, 0.29 mmol, 60% oil) in THF (9 mL), and the mixture was stirred at the same temperature for 15 minutes. Next, chloromethyl methyl ether (1.20 mL, 15.8 mmol) was added thereto, and the mixture stirred at room temperature for 45 minutes. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and isopropyl-(2-methoxymethoxy-1-methylethyl)amine (0.91 g; yield 54%) was thus obtained. 1H-NMR (CDCl3) δ(ppm): 1.05 (d, J=6.1 Hz, 3H), 1.06 (d, J=5.3 Hz, 3H), 1.08 (d, J=5.3 Hz, 3H), 2.94 (m, 2H), 3.36 (s, 3H), 3.38 (m, 1H), 3.47 (m, 1H), 4.63 (s, 2H).

1. stirringthe mixture stirred at room temperature for 45 minutes
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with a saturated saline solution
4. dry with materialdried over anhydrous sodium sulfate

ORD record

ord-f2d48c9713404f2a9f141e60b0d0ff8c

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953785B2