Hydrochloric Acid → HCID 86657329, compound

Temperature

-78 °C

Ethyl (6,7,8,9-tetrahydro-5H-5-benzocycloheptenyl)acetate (0.550 g) was dissolved in anhydrous toluene (10 ml), and the solution was slowly added with diisobutylaluminum hydride (0.93 M n-hexane solution, 2.8 ml) at −78° C. under an argon flow. The reaction mixture was stirred −78° C. for 1 hour, and then slowly added with methanol (3 ml) and 2 N aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate. 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: ethyl acetate:n-hexane=1:300) to obtain the title compound (0.432 g, yield: 97%).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed successively with water and saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationThe organic layer was concentrated under reduced pressure
5. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:300)

ORD record

ord-9c2dccd088af46f59371243a73e6c78a

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143260B2