Water → HCID 23001375, compound

Furfuryl alcohol (10.0 g, 102 mmol) was dissolved in DMF (200 ml) and sodium hydride (60% dispersion in oil, 9.00 g, 225 mmol) was added under ice-cooling. The mixture was stirred for 15 min at the same temperature. Then, 2-dimethylaminoethyl chloride hydrochloride (15.4 g, 107 mmol) was added under ice-cooling and the mixture was stirred at the same temperature for 30 min and at room temperature for 3.5 hr. Water (200 ml) was added to the reaction mixture under ice-cooling and the mixture was extracted with diethyl ether (2×500 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (20:1 chloroform-methanol) to give the title compound (4.19 g, 24%) as a red-brown liquid.

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred at the same temperature for 30 min and at room temperature for 3.5 hr
4. temperaturecooling
5. extractionthe mixture was extracted with diethyl ether (2×500 ml)
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customThe obtained residue was purified by silica gel column chromatography (20:1 chloroform-methanol)

ORD record

ord-542f5609d9da4c0bb722d54fb40d1943

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610729B1