Chlorotrimethylsilane → HCID 13387281, compound

Participants

Reaction Steps

A solution of 2,3-bis(4-fluorophenyl)furan (7.0 g, 27 mmoles) in 100 ml of dry dimethoxyethane was cooled to -35° and treated dropwise with n-butyl lithium (1.6M; 18.8 ml, 30 mmoles). The solution was stirred at -35° for one hour and treated with chlorotrimethylsilane (3.0 g, 27.6 mmoles). The reaction mixture was stirred at -35° for one hour and at room temperature for 24 hours. The mixture was concentrated in vacuo, suspended in 180 ml of carbon tetrachloride, and filtered through 50 g of silica gel. The filtrate was concentrated to an oil which crystallized on standing to yield 8.1 g (90%) of the title compound, m.p. 82°-83°. PMR (CDCl3) δ0.33 (s, 9H, Si(CH3)3); 6.87 (s, 1H, H--C=C--O), 6.9-7.8 (m, 8H, 2-p-FC6H4). MS: m/z 328.

Provenance & Evidence