HCID 368833, compound → HCID 368834, compound

HRID 1647315Notes

Reaction equation

HRID 1647315 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17](=O)[C:16]3[C:11](=[CH:12][C:13]([O:23][CH3:24])=[C:14]([O:21][CH3:22])[C:15]=3[O:19][CH3:20])[CH2:10]2)=[CH:5][CH:4]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:17][C:16]3[C:11](=[CH:12][C:13]([O:23][CH3:24])=[C:14]([O:21][CH3:22])[C:15]=3[O:19][CH3:20])[CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 368833HCID 368833, compound

Product 1

HCID 368834HCID 368834, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the ketone 34 (250 mg, 0.74 mmol) and 10% Pd-C (100 mg) in acetic acid (40 mL) was subjected to hydrogenolysis at 42 psi hydrogen pressure until the absorption of hydrogen ceased. Filtration and evaporation of the reaction solution gave an oil. It was purified by flash chromatography (ether:hexane, 70:30 by volume, silica gel 230-400 mesh) to afford 35 as a colorless oil(230 mg, 96.2%). TLC only showed one spot. 1H NMR (CDCl3, 500 MHz) δ7.22 (d, 2H, J=8 Hz), 6.72 (d, 2H, J=8 Hz), 6.59 (s, 1H), 3.90 (s, 3H), 3.88 (s, 3H), 3.84 (s, 3H), 3.80 (s, 3H), 3.63 (m, 1H), 3.36 (m, 1H), 3.26 (m, 1H), 2.97 (m, 2H). EIMS m/e 314 (M+, 100). Anal. (C19H22O4) C, H.

Workup

  1. customwas subjected to hydrogenolysis at 42 psi hydrogen pressure until the absorption of hydrogen
  2. filtrationFiltration and evaporation of the reaction solution
  3. customgave an oil
  4. customIt was purified by flash chromatography (ether:hexane, 70:30 by volume, silica gel 230-400 mesh)

Sources & evidence

ORD record
ord-44f3b727525f4d1e8f3a77f29cd0a24a
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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