HCID 58774160, compound → HCID 71254978, compound

HRID 714489Notes

Reaction equation

HRID 714489 reaction equation
[H][H].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH:22]([OH:23])[CH2:21][C:20]3[C:19]([OH:24])=[CH:18][C:17]([OH:25])=[CH:16][C:15]=3[O:14]2)=[CH:9][C:8]=1[OH:26])[CH:4]=[CH2:5]>[Pd].C(O)C>[OH:26][C:8]1[CH:9]=[C:10]([CH:13]2[CH:22]([OH:23])[CH2:21][C:20]3[C:19]([OH:24])=[CH:18][C:17]([OH:25])=[CH:16][C:15]=3[O:14]2)[CH:11]=[CH:12][C:7]=1[O:6][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 58774160HCID 58774160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71254978HCID 71254978, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of 10% palladium on carbon (5 mg, 10 mol %) in 5 mL ethanol which had been stirred vigorously under 1 atmosphere of hydrogen for 10 minutes then cooled with an ice/methanol bath was added a solution of 2-(4-Allyloxy-3-hydroxy-phenyl)-chroman-3,5,7-triol (50 mg) in 2 mL ethanol. The ice bath was removed and the reaction was stirred for 3 h under 1 atmosphere of hydrogen. The mixture was passed through a 0.22 micron nylon syringe filter and concentrated to a foam which was dissolved in acetonitrile/water, frozen, and lyophilized give 2-(3-Hydroxy-4-propoxy-phenyl)-chroman-3,5,7-triol as a white powder.

Workup

  1. temperaturethen cooled with an ice/methanol bath
  2. customThe ice bath was removed
  3. filtrationfilter
  4. concentrationconcentrated to a foam which
  5. dissolutionwas dissolved in acetonitrile/water
  6. temperaturefrozen

Sources & evidence

ORD record
ord-a2edcbac58f9418a994f9b9b6d948216
Source dataset
uspto-grants-2015_11
Patent number
US09187448B2

Reaction notes

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