Fluorene → HCID 19902687, compound

Participants

Reaction Steps

To a solution of 3.0 g (18.07 mmol) of fluorene in 50 mL of dry ether and 25 mL of freshly distilled THF was added dropwise 13 mL of 1.4M n-butyllithium. The mixture was refluxed for 3 hours, cooled to room temperature, and treated with 3 mL (14.02 mmol) of triisopropylsilyl chloride in one portion. The mixture was refluxed for 3 days, cooled to room temperature, and washed with sat'd NH4Cl (2×50 mL) and water (50 mL). The organic layer was dried over MgSO4 and the solvent was evaporated in vacuo to give an oil which was triturated with methanol to afford 3.34 g (73.8%) of the crude silane as a yellowish solid. Recrystallization from EtOH gave 2.98 g (65.9%) of 9-triisopropylsilylfluorene as white needles, m.p. 122°-123° C.; 1H NMR (CDCl3): δ 0.91 (d, 18H, Si-C-Me2), 1.09-1.42 (hept, 3H, Si-CH-Me2 , 4.26 s, 1H, ArCHAr), 7.05-8.00 (m, 8H, aryl).

Provenance & Evidence