Tetrahydrofuran → HCID 18423003, compound

Temperature

30 °C

To a suspension of aluminum lithium hydride (5.31 g) in tetrahydrofuran (500 ml) was added dropwise a solution of (4-azidomethylphenyl) methyl ketone (8.18 g) in tetrahydrofuran (100 ml) at below 5° C. over 30 min. The mixture was stirred at 30° C. for 2 hr. A saturated aqueous sodium sulfate solution (30 ml) was added and the mixture was stirred for 1 hr. The insoluble matter was filtered off and the solvent was evaporated. The obtained residue was dissolved in ethyl acetate (100 ml), 2N aqueous sodium hydroxide solution (30 ml) and water (70 ml). Thereto was added dropwise acetic anhydride (4.8 ml) with vigorous agitation at 10-15° C. over 10 min. The mixture was stirred at room temperature for 1 hr. The organic layer was separated and the aqueous layer was extracted with ethyl acetate and combined with the organic layer. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (elution solvent; methanol:chloroform=3:97, later 5:95) to give the title compound (5.37 g) as a rather brown oil.

1. stirringthe mixture was stirred for 1 hr
2. filtrationThe insoluble matter was filtered off
3. customthe solvent was evaporated
4. dissolutionThe obtained residue was dissolved in ethyl acetate (100 ml)
5. additionThereto was added dropwise acetic anhydride (4.8 ml) with vigorous agitation at 10-15° C. over 10 min
6. stirringThe mixture was stirred at room temperature for 1 hr
7. customThe organic layer was separated
8. extractionthe aqueous layer was extracted with ethyl acetate
9. washThe organic layer was washed with saturated brine
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was evaporated
12. customthe obtained residue was purified by silica gel column chromatography (
13. washelution solvent

ORD record

ord-e00be56bc76b4209ac3af4e0cafc542d

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455528B1