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

Participants

Reaction Steps

Under an argon stream, CH2Cl2 solvent (0.1 ml) was placed in a flask beforehand, and thereto were added dropwise, at 0 to 5° C., a mixed solution of dimethyl cis-9-octadecenedioate (141 mg, 0.41 mmol) and Bu3N (230 mg, 1.24 mmol) in CH2Cl2 (1.7 ml) and a solution of TiCl4 (132 μl, 1.20 mmol) in CH2Cl2 (2.0 ml) at the same time over a period of 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 (57 mg, 45%) and a by-product (34-membered ring; 22 mg, 17%).

Provenance & Evidence