Cyclopropyl methyl ketone → HCID 18950329, compound

Participants

Reaction Steps

Methanol (2 drops) was added to a mixture of sodium hydride (0.9 g) and tetrahydrofuran heated under reflux conditions. A mixture of methyl 4-chloro-3-ethylsulphenylmethyl-2-methylsulphenylbenzoate (4.0 g) and methyl cyclopropyl ketone (2.5 g) in tetrahydrofuran (36 ml) was added during 0.5 hours whilst maintaining at reflux. The mixture was stirred overnight at ambient temperature, and then quenched with methanol. Ether and water were added and the aqueous layer acidified (dilute hydrochloric acid), extracted (ether) and the ethereal solution extracted (sodium carbonate solution). This basic extract was re-acidified (hydrochloric acid), extracted (ether) and evaporated to give 4-chloro-3-ethylsulphenylmethyl-2-methylsulphenylbenzoic acid (3.0 g), NMR (CDCl3) 1.35 (t,3H), 2.5 (s,3H), 2.7 (q,2H), 4.3 (s,2H), 7.5 (d,1H), 7.8 (d,1H).

Provenance & Evidence