HCID 15233852, compound → HCID 18964034, compound

Participants

Reaction Steps

4-methoxy-4-[3-methyl-3-((napth-2yl)methoxy)-trans-prop-1-enyl]tetrahydropyran (320 mg, 1.02 mmol), prepared as in Example 3, was hydrogenated over palladium on calcium carbonate, poisoned with lead, with hydrogen (1 atm) in ethyl acetate at ambient temperature for 18 hours. After flushing the reaction solution with nitrogen, the solution was filtered through a pad of celite. The filter cake was thoroughly rinsed with ethyl acetate. The combined filtrates were concentrated in vacuo and chromatographed on silica gel (14 g, 15% ethyl acetate:hexanes) to provide the title compound (214 mg, 66%) as a colorless oil. 1H NMR (300 MHz, CDCl3); 7.75-7.87 (4H, m), 7.43-7.53 (3H, m), 4.67 (2H, s), 3.68 (4H, d,d, J=8,3 Hz), 3.52 (2H, t, J=6 Hz), 3.17 (3H, s), 1.49-1.78 (8H, m); MS (M+H)+ =315 , (M+NH4)+ =332. Analysis calc'd for C20H26O3 : C, 76.40; H, 8.33; Found: C, 76.30; H, 8.12.

Provenance & Evidence