4-Methyl-1,7-diphenyl-1,6-heptadiene-3,5-dione → 4-Methyl-1,7-diphenylheptane-3,5-dione

HRID 77644Notes

Reaction equation

HRID 77644 reaction equation
[CH3:1][CH:2]([C:13](=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3](=[O:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>[Pd].C(OCC)(=O)C>[CH3:1][CH:2]([C:3](=[O:12])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:13](=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 695017264-Methyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

Product 1

HCID 695017724-Methyl-1,7-diphenylheptane-3,5-dioneYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Methyl-1,7-diphenyl-1,6-hetpadiene-3,5-dione (6b, 0.96 g, 3.3 mmol) and palladium on activated carbon (0.25 g, 10%) were combined in ethyl acetate (50 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 2 hr at room temperature. The resulting mixture was filtered through celite and the filtrate was washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford an oil. The crude oil was twice chromatographed on silica gel with ethyl acetate/hexane to give an oil. The oil was distilled bulb to bulb to give 0.71 g (73%) of a clear oil; 1H NMR: δ enol form: 1.66 (s, 3H), 2.73 (m, 8H), 7.17 (m, 10H); keto form: 1.20 (d, 3H, J=7.2 Hz), 2.73 (m, 8H), 3.55 (q, 1H, J=7.0 Hz), 7.17 (m, 10H); 13C NMR: δ 12.3, 29.3, 31.0, 37.6, 42.8, 60.9, 104.2, 125.9, 128.1, 128.2, 140.4, 140.8, 174.6, 191.5, 205.6; Exact mass calcd for C20H22O2: 294.1620, observed (M+H) 295.1693.

Workup

  1. customfor 2 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. washthe filtrate was washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an oil
  9. customThe crude oil was twice chromatographed on silica gel with ethyl acetate/hexane
  10. customto give an oil
  11. distillationThe oil was distilled bulb to bulb

Sources & evidence

ORD record
ord-5ba5e6758e0847e2b39eb70ee3868ed4
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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