Furfuryl Alcohol → HCID 9833973, compound

To a mixture of sodium hydride (7.7 g, 190 mmol, 60% in oil) and tetrahydrofuran (100 mL) was added dropwise furfuryl alcohol (15 mL, 170 mmol) at 0° C. The reaction mixture was warmed to room temperature, N,N-dimethylformamide (30 mL) was added at that temperature, and the mixture was stirred at that temperature for 30 minutes. The reaction mixture was returned to 0° C., propargyl bromide (23 g, 190 mmol) was added at that temperature, and the mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with brine, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:30) to give the title compound (7.6 g, 32% yield).

1. customwas returned to 0° C.
2. stirringthe mixture was stirred for 1 hour at room temperature
3. extractionwas then extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. distillationthe solvent was distilled away under reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:30)

ORD record

ord-1f4e7423c2024bbd9b0489e2230499e7

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933100B2