Hexane → 1H-Indene, 2-methyl-

Temperature

-78 °C

The ligand (1.0 g) obtained from the previous procedure was dissolved in anhydrous tetrahydofuran (40 ml) and a solution of n-butyllithium in hexane (1.6M, 4.4 ml) was and stirred for 3 hours. The solvents were removed under vacuum to obtain a off-white solid which was washed with dry hexane under nitrogen atmosphere. The solid was cooled to −78° C. and methylene chloride prechilled to −78° C. was added followed by a slurry of zirconium tetrachloride in methylene chloride which was also prechilled to −78° C. The reaction mixture was allowed to gradually come to room temperature and stirred overnight. The solution was filtered and the solid was washed with hexane. The hexane washings were added to the filtrate at which time a off-white solid precipitated. Upon filtration the filtrate was concentrated and cooled to −78° C. for several hours to obtain a yellow solid. This yellow solid (0.30 g) was isolated by filtration and was found to be a mixture (65:35) of rac- and meso-isomers by NMR spectroscopy. 1HNMR (CD2Cl2) (in ppm), 7.67(2d), 7.45(d), 7.08(t), 6.99(t), 6.76(s), 6.74(s), 6.64(s), 2.44(s), 2.20(s), 1.42(s), 1.29(s), 1.22(s). The solid was used as such in polymerizations.

1. customThe solvents were removed under vacuum
2. customto obtain a off-white solid which
3. washwas washed with dry hexane under nitrogen atmosphere
4. customprechilled to −78° C.
5. additionwas added
6. customwas also prechilled to −78° C
7. customto gradually come to room temperature
8. stirringstirred overnight
9. filtrationThe solution was filtered
10. washthe solid was washed with hexane
11. additionThe hexane washings were added to the filtrate at which time a off-white solid
12. customprecipitated
13. filtrationUpon filtration the filtrate
14. concentrationwas concentrated
15. temperaturecooled to −78° C. for several hours
16. customto obtain a yellow solid

ORD record

ord-91f027f85a184e108bbc10d85c2641a5

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262199B1