HCID 89405842, compound → HCID 53462609, compound

HRID 714490Notes

Reaction equation

HRID 714490 reaction equation
[H][H].[CH2:3]([O:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:25]CC3C=CC=CC=3)=[CH:13][C:14]=2[O:17]CC2C=CC=CC=2)[O:9][CH:8]1[C:33]1[CH:38]=[CH:37][C:36]([O:39]CC2C=CC=CC=2)=[C:35]([O:47]CC2C=CC=CC=2)[CH:34]=1)[CH:4]=[CH2:5]>[Pd].C(OCC)(=O)C.C(O)C>[OH:47][C:35]1[CH:34]=[C:33]([CH:8]2[CH:7]([O:6][CH2:3][CH2:4][CH3:5])[CH2:16][C:15]3[C:14]([OH:17])=[CH:13][C:12]([OH:25])=[CH:11][C:10]=3[O:9]2)[CH:38]=[CH:37][C:36]=1[OH:39]

Participants

5

Reactant 2

HCID 89405842HCID 89405842, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53462609HCID 53462609, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a suspension of 20% palladium on carbon (80 mg) in 1:1 ethyl acetate/ethanol (15 mL) which had been stirred vigorously under 1 atmosphere of hydrogen for 10 minutes then cooled with an ice/methanol bath was added 3-Allyloxy-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman (200 mg). The ice bath was removed and the reaction was stirred for 2 h under 1 atmosphere of hydrogen. The mixture was filtered and concentrated, and purified by preparative reverse phase HPLC using a gradient of 5% to 100% acetonitrile/water over 10 min The appropriate fractions were frozen and lyophilized to yield 2-(3,4-Dihydroxy-phenyl)-3-propoxy-chroman-5,7-diol as a white powder.

Workup

  1. temperaturethen cooled with an ice/methanol bath
  2. customThe ice bath was removed
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. custompurified by preparative reverse phase HPLC
  6. customover 10 min
  7. temperaturewere frozen

Sources & evidence

ORD record
ord-75bf4c21bb9d46668a3c15ae5a175d78
Source dataset
uspto-grants-2015_11
Patent number
US09187448B2

Reaction notes

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