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0 °C

15.0 g (54 nunol) of CH2(1-indanone)2, prepared as described above, and 24.3 g (2.4 equiv.) of tosyl hydrazine were placed in a 250 ml round-bottom flask and 100 ml EtOH added. Then 10 drops of 37% HCl were added and the reaction mixture brought to reflux under nitrogen. On coming to reflux, everything dissolved and a clear brown solution resulted. After refluxing for 10 minutes, a white jelly-like material began to precipitate. This was washed with MeOH and then dried under vacuum. This gave 21 g (63%) of the bis(hydrazone). 10.8 g (17.6 mmol) of the bis(hydrazone), suspended in 250 ml N,N,N′,N′-tetramethyl-ethylene diamine (TMEDA) in a large Schlenk tube, was slowly added to 15.2 g (141 mmol, 8 equivalents) of lithium diisopropylamide, dissolved in 50 ml TMEDA and cooled to 0° C. The solution changed from yellow to purple and then to dark purple. It was allowed to warm to room temperature and then decanted onto ice to give a yellow solution. On washing with 100 ml aqueous NaHCO3 the solution became purple. This was extracted copiously (3×250 ml) with Et2O, the Et2O extracts combined and dried over MgSO4. These were evaporated to a brown oil which was extracted with pentane. Working up of the pentane extracts afforded 0.59 g (14%) of bis(2-indenyl)methane.

1. customwere placed in a 250 ml round-bottom flask
2. temperatureto reflux under nitrogen
3. temperatureto reflux
4. dissolutioneverything dissolved
5. customa clear brown solution resulted
6. temperatureAfter refluxing for 10 minutes
7. customto precipitate
8. washThis was washed with MeOH
9. customdried under vacuum
10. temperatureto warm to room temperature
11. customdecanted onto ice
12. customto give a yellow solution
13. washOn washing with 100 ml aqueous NaHCO3 the solution
14. extractionThis was extracted copiously (3×250 ml) with Et2O
15. dry with materialdried over MgSO4
16. customThese were evaporated to a brown oil which
17. extractionwas extracted with pentane