Fluorene → HCID 67259085, compound

Participants

Reaction Steps

A 2.5 M n-BuLi solution in hexane (9.6 mL) was added dropwise at 0° C. under stirring to a solution of 3.78 g of fluorene in 40 ml of Et2O in a 100 mL Schlenk flask. After 30 min the resulting orange solution was allowed to warm up to room temperature and stirred for 3 days. A solution of chloro(2,4,6-trimethylindenyl)dimethylsilane (22.60 mmol) in 20 mL of THF was cooled to 0° C. and slowly added to the lithium salt solution, also previously cooled to 0° C. At the end of the addition a light brown suspension was obtained. The latter was allowed to warm up to room temperature and stirred for 24 h. Then the reaction mixture was evaporated under reduced pressure to give a brown sticky solid, which was treated at r.t. with 50 mL of toluene and then filtered to remove LiCl. The filtrate was dried in vacuo to give 8.54 g of a brown oil. The product was characterized by 1H-NMR spectroscopy: there are the signals of two isomeric species: allylic and vinylic (2:1). The product was used as such in the next step without further purification.

Provenance & Evidence