Phenoxodiol → (R,S)-Equol

HRID 1891430Notes

Reaction equation

HRID 1891430 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][O:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([OH:18])[CH:12]=3)=[CH:4][CH:3]=1>CO.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][C:13]([OH:18])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 219100Phenoxodiol

Product 1

HCID 382975(R,S)-Equol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-hydroxy-phenyl)-2H-chromen-7-ol (P7) (0.241 g, 1 mmol) in MeOH was added 10% Pd—C (0.050 g). This reaction mixture was hydrogenated at room temperature under 2 atm (30 psi) of H2 pressure for ca. 6 hours. After the disappearance of starting material (TLC), the catalyst was filtered through a pad of celite. The celite-pad was washed with 10 mL of THF then 2×10 mL of MeOH. The solution was filtered once more through filter paper and evaporated to obtain the brownish solid residue which was chromatographed over silica gel using CH2Cl2:MeOH (6:1) to get (0.169 g, 70%) reddish white solid P8. 1H NMR (600 MHz, Acetone-d6) δ,7.08 (d, 2H, J=8.4 Hz, Ar—H2′/H6′), 6.82 (d, 1H, J=7.8 Hz, Ar—H5), 6.80 (d, 2H, J=8.4 Hz, Ar—H3′/H5′), 6.35, (dd, 1H, 2J=7.8 Hz, 3J=2.4 Hz), 6.27 (d, 1H, 3J=2.4 Hz), 4.15 (m, 1H, O—CH), 3.88 (t, 1H, J=10.8 Hz, O—CH), 3.0 (m, 1H, 3-CH), 2.9 (m, 2 H, 4-CH2).

Workup

  1. filtrationAfter the disappearance of starting material (TLC), the catalyst was filtered through a pad of celite
  2. washThe celite-pad was washed with 10 mL of THF
  3. filtrationThe solution was filtered once more
  4. filtrationthrough filter paper
  5. customevaporated
  6. customto obtain the brownish solid residue which
  7. customwas chromatographed over silica gel
  8. customto get (0.169 g, 70%)

Sources & evidence

ORD record
ord-d7af4d2e59c34c2e8d272914aeb30b76
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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