Potassium Hydroxide → HCID 70386242, compound

The keto-diester (16) (30 mg, 0.06 mmole) was added to a degassed 10% solution of potassium hydroxide in methanol-water (19:1) (4 ml), and the solution was boiled for 3.5 h under nitrogen. The solvent was removed by evaporation under reduced pressure, and the residue was dissolved in ether. The residue 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 (5) (16 mg, 82%), m.p. 113°-4° C. (from ether-light petroleum), νmax 3400 (OH) and 1675 cm-1 (CO), δ (400 MHz) 8.08 (1 H, dd, J 8.5 and 1 Hz, 1-proton), 7.54 (1 H, d, J 3 Hz, 4-proton), 7.12 (1 H, dd, H 8.5 and 3 Hz, 2-proton), 4.27 (1 H, dt, H 10 and 5 Hz, 11-proton), 3.85 (3 H, s, OCH3), 3.79 (1 H, t, J 8 Hz, 17-proton), 2.78 (1 H, dd, J 17 and 2,5 Hz, 12-proton), 2.45 (1 H, t, J 10 Hz, 9-proton), 2.35 (1 H, A portion of ABX system, J 12 and 5 Hz, 7-proton), 2.35 (1 H, B portion of ABX system, J 12 and 5 Hz, 7-proton), 2.18 (2 H, m), 1.96 (1 H, qt, J 14, 10, 5, and 3.5 Hz, 8-proton), 1.86 (2 H, br s, OH), 1.56-1.27 (5 H, m), 0.8 (3 H, s, 18-CH3);

1. customThe solvent was removed by evaporation under reduced pressure
2. dissolutionthe residue was dissolved in ether
3. washThe residue was washed in succession with dilute hydrochloric acid and water
4. customdried
5. customevaporated
6. customto give a residue which
7. customwas chromatographed on silica (1 g)
8. washeluted with ether

ORD record

ord-7712f60833204300a7a646e0d126cdf5

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04882439