Sodium borohydride → HCID 12322894, compound

Temperature

0 °C

A solution of 2,3,3a,4,5,6-hexahydro-phenalene-1-one (2.00 g) in anhydrous tetrahydrofuran (70 ml) was cooled to 0° C., and slowly added with sodium borohydride (1.62 g) and aluminum chloride (2.85 g). The reaction mixture was refluxed by heating for 3 hours, then cooled to 0° C., and diluted with ethyl acetate. The reaction mixture was slowly added with ice until foaming ceased, and then the mixture was made to be at room temperature and stirred overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane) to obtain the title compound (1.47 g, yield: 80%).

1. temperatureThe reaction mixture was refluxed
2. temperatureby heating for 3 hours
3. additionThe reaction mixture was slowly added with ice until foaming
4. customto be at room temperature
5. extractionThe reaction mixture was extracted with ethyl acetate
6. washthe organic layer was washed successively with water and saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationThe organic layer was concentrated under reduced pressure
9. customthe resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane)

ORD record

ord-c1f27831c43d49ec80ef9d996a7cc3a6

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143260B2