Benzene → HCID 66811298, compound

Temperature

0 °C

A suspension of sodium hydride (60%, 0.130 g) in anhydrous benzene (5 ml) was slowly added with diethyl phosphonoacetate (0.750 g) at 0° C., and the mixture was stirred at 0° C. for 10 minutes. The mixture was added with a solution of (6,7,8,9-tetrahydro-5H-5-benzocycloheptenyl)acetaldehyde (0.419 g) in anhydrous benzene (5 ml), and the mixture was stirred at 0° C. for 5 minutes, and then refluxed overnight by heating. The reaction mixture was left to cool and then added with saturated aqueous ammonium chloride, 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 (0.544 g, yield: 94%).

1. stirringthe mixture was stirred at 0° C. for 5 minutes
2. temperaturerefluxed overnight
3. temperatureby heating
4. waitThe reaction mixture was left
5. temperatureto cool
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic layer was washed successively with water and saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationThe organic layer was concentrated under reduced pressure
10. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:300)

ORD record

ord-69550cffefe04b2d858ac4579850021d

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232300B2