Carbon Dioxide → HCID 59317564, compound

Temperature

-78 °C

1,2,3,4-tetrahydroquinoline (957 mg, 7.185 mmol) was dissolved in THF (10 mL), and the resultant solution was stirred at −78° C. for 30 minutes. Then, n-BuLi (2.87 mL, 7.185 mmol) was added with a syringe in the nitrogen atmosphere. The resultant solution was heated up to the room temperature and stirred sufficiently for 3 hours. The solution was cooled down to −78° C. again, and CO2 gas was added to initiate a reaction. The solution was heated up to the room temperature and stirred to eliminate the remaining CO2 gas. Tert-butyl lithium (BuLi) (5.07 mL, 8.622 mmol) was added at −20° C. After sufficient 2-hour agitation still at −20° C., a 0.33 M solution of CeCl3.2LiCl (26.1 mL, 8.622 mmol) in THF and tetramethyl cyclopentenone (1.182 g, 8.622 mmol) were added in the nitrogen atmosphere. While slowly heated up to the room temperature, the resultant solution was vented, removed of the solvent, and then subjected to extraction with water and ethyl acetate. The organic phase thus formed was separated and removed of the solvent. Then, 8-(2,3,4,5-tetramethyl-1,3-cyclopentadienyl)-1,2,3,4-tetrahydroquinoline was obtained through column chromatography (41% yield).

1. customa reaction
2. temperatureThe solution was heated up to the room temperature
3. stirringstirred
4. waitAfter sufficient 2-hour agitation still at −20° C.
5. temperatureWhile slowly heated up to the room temperature
6. customremoved of the solvent
7. extractionsubjected to extraction with water and ethyl acetate
8. customThe organic phase thus formed
9. customwas separated
10. customremoved of the solvent

ORD record

ord-1e804f97c7254afe9cbc5acbda092c81

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056939B2