Glycerol → HCID 89052022, compound

Temperature

50 °C

0.27 g (55%, 6.2 mmol) of sodium hydride was added to a solution of glycerol 0.57 g (6.2 mmol) in dry N,N-dimethylformamide (6 mL) with cooling on ice. After the mixture was stirred for 30 min at 50° C., the above (4,8,12-trimethyltridec-3-enyl)tosylate was added dropwise, with additional stirring for 10 hours at the same temperature. After addition of water at 0° C., the reaction mixture was extracted with ethyl acetate. The extract was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane mixture) to obtain 79 mg of the title compound (6% yield in 2 steps). The results of NMR analysis of the obtained compound are as shown below.

1. temperaturewith cooling on ice
2. stirringwith additional stirring for 10 hours at the same temperature
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe extract was washed with water, 1M hydrochloric acid, saturated sodium bicarbonate aqueous solution, and saturated brine
5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated
8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane mixture)

ORD record

ord-2fe8dd120b3e4a0db01d5cbdcff2e82f

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703922B2