Potassium Hydroxide → HCID 70385933, compound

Participants

Reaction Steps

The keto-diester (23) (21 mg, 0.05 mmole) was added to a degassed 10% solution of potassium hydroxide in methanol-water (19:1) (4 ml), and the solution was boiled for 15 min under nitrogen. The solvent was removed by evaporation under reduced pressure, and the residue was dissolved in ether. The extract was washed in succession with dilute hydrochloric acid and water, dried, and evaporated to give a residue which was chromatographed on silica (1 g) eluted with ether to give the product (6A) (15 mg, 90%), m.p. 225°-6° C. (from ether-light petroleum), νmax 3460 (OH) and 1655 cm-1 (CO), δ (250 MHz) 7.61 (1 H, d, J 2.5 Hz, 4-proton), 7.37 (1 H, d, J 8 Hz, 1-proton), 7.17 (1 H, dd, J 8 and 2.5 Hz, 2-proton), 4.84 (1 H, dt, H 3 and 2.5 Hz, 11-proton), 3.85 (3 H, s, OCH3), 3.74 (1 H, dd, J 9 and 7 Hz, 17-proton) 2.78 (1 H, dd, J 15 and 2.5 Hz, 12-proton), 2.71 (1 H, dd, J 10.5 and 2.5 Hz, 9-proton), 2.44 (10 H, m), 1.04 (3 H, s, 18-CH3);

Provenance & Evidence