HCID 15233852, compound → HCID 18964034, compound

HRID 326231Notes

Reaction equation

HRID 326231 reaction equation
[CH3:1][O:2][C:3]1(/[CH:9]=[CH:10]/[CH:11](C)[O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1([CH2:9][CH2:10][CH2:11][O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 15233852HCID 15233852, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18964034HCID 18964034, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customAfter flushing the reaction solution with nitrogen
  2. filtrationthe solution was filtered through a pad of celite
  3. washThe filter cake was thoroughly rinsed with ethyl acetate
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customchromatographed on silica gel (14 g, 15% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a5e6bad3533b48b2978d13c2ce3daa34
Source dataset
uspto-grants-1993_12
Patent number
US05268379

Reaction notes

Loading…