Hydrochloric Acid → HCID 58812147, compound

Participants

Reaction Steps

A mixture of 1-(2-chloro-ethoxy)-3-nitrobenzene (1.12 g, 5.6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (1.6 g, 6.72 mmoles) was stirred in THF (50 mL) at −78° C., in a round bottom flask under nitrogen. A solution of 1M potassium t-butoxide was added dropwise (16.8 mL, 16.8 mmoles) over a half an hour period. Temperature was allowed to rise to −40° C., and the reaction mixture was stirred at this temperature for 5 hours. The reaction mixture was poured into cold 2N HCl, extracted with EtOAc, dried over Na2SO4, and concentrated under vacuum. Compound was purified by normal phase HPLC using as eluent 40% EtOAc/hexane to afford the title compound as an off-white solid (0.9 g, 2.24 mmoles), and 1-[4-(2-chloro-ethoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene (0.79 g, 2.1 mmoles).

Provenance & Evidence