Water → Methyl 17-oxocycloheptadec-8-ene-1-carboxylate

Participants

Reaction Steps

Under an argon stream, to a suspension of ZrCl4 (338 mg, 1.45 mmol) in CH2Cl2 (1.0 ml) were added dropwise, at 0 to 5° C., a mixed solution of dimethyl cis-9-octadecenedioate (170 mg, 0.50 mmol) and Bu3N (278 mg, 1.50 mmol) in CH2Cl2 (4.0 ml) over a period of about 1 hour by means of a microfeeder. The whole was further mixed at the same temperature for 15 minutes. Water was added to the reaction mixture and the resulting mixture was stirred and then extracted with ether. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. After the evaporation of the solvent under reduced pressure, the crude product was purified by silica gel chromatography (hexane/ethyl acetate=20/1→10/1) to obtain the aimed product (43 mg, 28%) and a by-product (34-membered ring; 6 mg, 4%).

Provenance & Evidence