Acetyl chloride → (RS) alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-oxo-3-methoxymethyl-1-propynyl)-cyclopropane-carboxylate

Participants

Reaction Steps

A solution of 3 g of (RS)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-hydroxy-3-oxo-1-propynyl)-cyclopropane-carboxylate in 30 ml of anhydrous dimethylformamide was cooled to +10° C. and 300 mg of 61% sodium hydride in oil were added in portions thereto. Then, over 15 minutes, 2.5 ml of chloromethyl ether solution prepared by mixing 4.5 ml of methylal and 0.52 ml of methanol and slowly adding 3.53 ml of acetyl chloride after which the mixture was stirred for 36 hours at room temperature. The mixture was stirred for 2 hours and was then poured into an aqueous solution of monosodium phosphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 75-25 mixture of cyclohexane-ethyl acetate to obtain 2 g of (RS) α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(3-oxo-3-methoxymethyl-1-propynyl)-cyclopropane-carboxylate.

Provenance & Evidence