Chlorotrimethylsilane → HCID 11255491, compound

Participants

Reaction Conditions

Reaction Steps

A cooled (0°-5° C.) solution of 41.4 g (0.41 mol) of diisopropylamine in 300 ml of tetrahydrofuran was treated slowly with butyllithium in hexane (250 ml of a 1.6 M solution, 0.4 mol). A solution of 34.12 g (0.2 mol) of p-chlorophenylacetic acid in 200 ml of tetrahydrofuran was added dropwise and the reaction mixture was stirred 30 minutes at 0° C. Trimethylchlorosilane (100 g) was added and the mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The contents of the flask were filtered under nitrogen and the filtrate was evaporated under reduced pressure. The residue was dissolved in 80 ml of diethyl ether; the solution was filtered and the filtrate was evaporated. The resultant residue was distilled in a Vigreux column, maintaining the pot temperature below 130° C. to prevent decomposition of the product. The product β,β-bis(trimethylsiloxy)p-chlorostyrene, 32.56 g (52% yield), was obtained as a colorless liquid, bp 110° C. (0.1 mm); 1H NMR (CDCl3) δ7.0-7.4 (m, 4H), δ4.52 (s, 1H); δ0.22 (s) and δ0.26 (s) together 18H. The moisture sensitive product was stored under nitrogen.

Provenance & Evidence