Hydrochloric Acid → HCID 69269859, compound

Participants

Reaction Steps

Slurry (methoxymethyl)triphenylphosphonium chloride (32.3 g, 93.7 mmol) in tetrahydrofuran (350 ml) and cool in an ice-water bath. Add 1.0M KOtBu (94 ml, 94 mmol) in tetrahydrofuran solution to the reaction dropwise via an addition funnel. Stir reaction for one hour, then add 5-chloro-2-nitrobenzaldehyde (14.5 g, 78.1 mmol) dropwise as a solution in 100 ml tetrahydrofuran. Continue to stir in the ice bath for 20 minutes, then let warm to ambient temperature. Quench with 0.1 N HCl, extract with ethyl acetate, wash organics with water and brine. Dry with sodium sulfate, filter, concentrate to a brown oil. Purify by flash chromatography (1% EtOAc:Hexanes) to give a crude mix of three spots. Dissolve the crude oil in methanol (200 ml), cool in an ice bath, add 4N HCl in dioxane (30 ml), stir overnight, warming to ambient temperature. Concentrate to brown oil. Purify by flash chromatography, elute with hexanes to 3% EtOAc:hexanes gradient. Yields the title compound (3.7 g, 15.1 mmol, 19%).

Provenance & Evidence