HCID 59014506, compound → HCID 11517219, compound

HRID 1992995Notes

Reaction equation

HRID 1992995 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)=[C:7]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[C:6]([CH3:31])=[CH:5]2>[Pd].CCOC(C)=O.CCO>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)=[C:7]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[C:6]([CH3:31])=[CH:5]2

Participants

4

Reactant 1

HCID 59014506HCID 59014506, compound

Product 1

HCID 11517219HCID 11517219, compoundYield 434.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A 1:1 EtOAc/EtOH solution (4 mL) of (2E)-3-(4-{[6-hydroxy-2-(3-hydroxyphenyl)-3-methyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (251) (0.041 g, 0.01 mmol, 1 equiv) was treated with 5% Pd—C (0.027 g, 0.02 mmol, 0.1 equiv) and the reaction vessel was equipped with an H2-filled balloon. After 14 h at ambient temperature, the crude mixture was filtered through a pad of Celite. Concentration gave a light pink solid that was purified by radial chromatography (SiO2, 1 mm plate, 90:10; CHCl3/MeOH) to afford the title compound (252) as a pink solid (0.018 g, 44%). 1H NMR (CD3OD, 400 MHz) δ 7.58 (d, J=9.0 Hz, 1H), 7.40 (s, 1H), 7.07-7.03 (m, 2H), 6.95-6.89 (m, 3H), 6.62 (dd, J=8.1, 2.3 Hz, 1H), 6.55-6.52 (m, 2H), 6.43 (d, J=8.5 Hz, 2H), 2.75 (t, J=7.7 Hz, 2H), 2.34 (t, J=7.3 Hz, 2H), 2.17 (s, 3H).

Workup

  1. customthe reaction vessel was equipped with an H2-
  2. additionfilled balloon
  3. filtrationthe crude mixture was filtered through a pad of Celite
  4. concentrationConcentration
  5. customgave a light pink solid
  6. customthat was purified by radial chromatography (SiO2, 1 mm plate, 90:10; CHCl3/MeOH)

Sources & evidence

ORD record
ord-c9313d17cf36481fa52602d3ffe78d3c
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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