Chloromethyl Methyl Ether → HCID 68898068, compound

4-methyl-quinoline-3-carbonitrile (600 mg, 3.567 mmol) was dissolved in 10 mL of anhydrous THF, added with LHMDS (1M solution in THF, 3.9 mL, 3.924 mmol) at −78° C. under the nitrogen atmosphere and then stirred for about 1 hour at the same temperature. The mixture was dropwisely added with chloromethyl methyl ether (0.30 mL, 3.924 mmol) and then stirred for about 1 hour at −50° C., and then for about 1 hour at 0° C. The above mixture, while being stirred at 0° C., was added with 5 mL of a saturated solution of ammonium chloride and 10 mL of distilled water and then extracted twice with 50 mL of EtOAc. The resulting organic layer was washed with a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. A silica gel column chromatography (30% EtOAc/Hexanes) was performed on the residue resulted by concentration of the above filtrate and obtained 305 mg (40%) of 4-(2-methoxy-ethyl)-quinoline-3-carbonitrile in pale yellow solid.

1. stirringstirred for about 1 hour at −50° C.
2. waitfor about 1 hour at 0° C
3. stirringThe above mixture, while being stirred at 0° C.
4. extractionextracted twice with 50 mL of EtOAc
5. washThe resulting organic layer was washed with a saturated solution of sodium chloride
6. dry with materialdried with anhydrous sodium sulfate
7. filtrationfiltered
8. customresulted by concentration of the above filtrate

ORD record

ord-578c4388bb5345b8b30ec1c140e19289

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601736B2