Chlorotrimethylsilane → HCID 15319840, compound

Participants

Reaction Steps

3.3 g of 2,2-bis(3-indenyl)propane (20511/46, MW 272.39, 12.11 mmol) and 50 m of THF in a 100 mL flask were cooled to -70° C. while stirring. 17 mL of a 1.6 M solution of BuLi (27.2 mmol) in hexane were added dropwise. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The solution was cooled again to -70° C. and 3.4 mL of Me3SiCl (MW 108.64, d 0.856, 26.8 mmol) were added. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 h. Water is then added, the organic layer is separated and the water layer extracted twice with Et2O, all organic phases were combined and dried over MgSO4, then filtered and all volatiles removed in vacuo. 4.8 g (95%) of a mixture of rac/meso 2,2-bis(1-trimethylsilyl-3-indenyl)propane was obtained. 1H NMR (200 MHz, C2D2Cl4, 120° C., referenced to the peak of residual C2HDCl4 at 5.75 ppm): 7.1-7.3 (m, 4H, C6 ring), 6.75-6.95 (m, 4H, C6 ring), 6.3-6.4 (br s, 2H, C5 ring), 3.2-3.3 (m, 2H, C5 ring), 1.64, 1.62 (2 s, 6H, bridge methyls), -0.15, -0.17 (2 s, 18H, TMS methyls).

Provenance & Evidence