HCID 69501646, compound → HCID 58769112, compound

HRID 77647Notes

Reaction equation

HRID 77647 reaction equation
[CH3:1][C:2]([CH3:23])([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][C:2]([CH3:23])([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 69501646HCID 69501646, compound

Product 1

HCID 58769112HCID 58769112, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4,4-Dimethyl-1,7-diphenyl-1,6-heptadiene-3,5-dione (11b, 0.15 g, 0.5 mmol) and palladium on activated carbon (0.20 g, 10%) were combined in ethyl acetate (25 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 1 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 chromatographed on silica gel with ethyl acetate/hexane to give 0.12 g (80%) of a pale yellow oil; 1H NMR: δ 1.25 (s, 6H), 2.60 (t, 4H, J=7.4 Hz), 2.80 (t, 4H, J=7.0 Hz), 7.18 (m, 10H); 13C NMR: δ 21.1, 29.8, 40.2, 62.4, 126.1, 128.3, 140.7, 208.4; Exact mass calcd for C21H24O2: 308.1776, observed (M+H) 309.1843.

Workup

  1. customfor 1 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 chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c6abe79f2d548b1a5b6e6db4ba09157
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

Loading…