Hexane → HCID 46836504, compound

HRID 1928688Notes

Reaction equation

HRID 1928688 reaction equation
C=CC[C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:16]([OH:17])=[C:15]([OH:18])[CH:14]=[C:13]([CH2:19][CH:20]=[CH2:21])[CH:12]=2)[CH:7]=[CH:6][CH:5]=1.[CH3:22][CH2:23][CH2:24]CCC>CO.C(OC(=O)C)C.[Pd](Cl)Cl>[CH:22](/[C:5]1[CH:4]=[CH:9][C:8]([O:10][C:11]2[CH:12]=[C:13](/[CH:19]=[CH:20]/[CH3:21])[CH:14]=[C:15]([OH:18])[C:16]=2[OH:17])=[CH:7][CH:6]=1)=[CH:23]\[CH3:24]

Participants

6

Reactant 2

HCID 8058HexaneHCID 45270574HCID 45270574, compound

Product 1

HCID 46836504HCID 46836504, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of obovatol (1 g) in methanol was added palladium chloride (PdCl2) (10 mg), followed by stirring at room temperature for 5 hours. After completion of the reaction, the organic layer containing the active material was collected and concentrated in a vacuum. The concentrate (1.1 g) was dissolved in methylene chloride (30 ml) and loaded onto a silica gel (Merck, Art No. 9385) so as to adsorb the active material thereonto. Purification through silica gel column chromatography eluting with a gradient of a mixture of ethylacetate and hexane from 10:90 to 20:80 afforded colorless 3-(4-((E)-prop-1-enyl)phenoxy)-5-((E)-prop-1-enyl)benzene-1,2-diol (0.91 g, yield 90%)

Workup

  1. customAfter completion of the reaction
  2. additionthe organic layer containing the active material
  3. customwas collected
  4. concentrationconcentrated in a vacuum
  5. concentrationThe concentrate (1.1 g)
  6. dissolutionwas dissolved in methylene chloride (30 ml)
  7. customPurification through silica gel column chromatography

Sources & evidence

ORD record
ord-480bbf90e32b407cbc06aaa8e6899035
Source dataset
uspto-grants-2012_05
Patent number
US08183405B2

Reaction notes

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