Water → 7-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of trimethylsulphonium iodide (7.66 g, 37.54 mmol) in dry DMSO (50 ml), under nitrogen was added 50% sodium hydride (1.8 g, 37.54 mmol). The solution was cooled to 10° C. A suspension of 3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-benzaldehyde 29 (10.0 g, 34.12 mmol) in THF (50 ml) was added to the above solution in one portion. The reaction mixture was stirred at ambient conditions for 2 hours and poured into water (1.0 L) followed by usual work in ethyl acetate, and FC to give the epoxide 30 (7.0 g, 66%) as a cream colored solid.

Provenance & Evidence