Isopropanol → HCID 15003279, compound

Participants

Reaction Steps

To a solution of 3.15 g of the crude alcohol 27 (prepared in 30-(3)) in 80 ml of acetone is added 10 ml of 8N Jones' reagent at 20° C. to 30° C. dropwise. The mixture is stirred for additional 10 minutes, and 3 ml of isopropyl alcohol is added thereto. The resulting mixture is stirred for 10 minutes and acetone is evaporated under reduced pressure. Water is added to the residue, and the residue is extracted with ethyl acetate twice. The organic layer is washed with water and then extracted with 1N aqueous solution of sodium hydroxide. The aqueous layer is acidified to pH 2 with hydrochloric acid and extracted with ethyl acetate again. The ethyl acetate extract is washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue is dissolved in 50 ml of ether and an ethereal solution of diazoethane is added at 0° C. until the orange color persists. The reaction mixture is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel (50 of silica gel, ethyl acetate-n-hexane=1:19) to give 2.35 g of the desired ethyl ester 28 as an oil in 67.0% yield from the compound 26.

Provenance & Evidence