HCID 66745084, compound → HCID 46218705, compound

HRID 386847Notes

Reaction equation

HRID 386847 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[C:23]1(O)[CH2:27][CH2:26][O:25][CH2:24]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[O:25]1[CH2:26][CH2:27][CH:23]([C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[OH:8])[CH2:24]1

Participants

4

Reactant 1

HCID 66745084HCID 66745084, compound

Product 1

HCID 46218705HCID 46218705, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.56 g of 3-(2,4-bis(benzyloxy)-phenyl)tetrahydrofuran-3-ol in 25 ml of ethyl acetate, in the presence of 780 mg of palladium-on-charcoal at 10%, is stirred at ambient temperature under a hydrogen pressure of 5 bar for 7 hours. The reaction medium is filtered and then the filtrate is evaporated. The residue is chromatographed on silica gel, elution being carried out with 50/50 heptane/ethyl acetate. The solid obtained is crystallized from dichloromethane/heptane. 285 mg of 4-(tetrahydrofuran-3-yl)benzene-1,3-diol are obtained in the form of a white powder. Yield=36%.

Workup

  1. filtrationThe reaction medium is filtered
  2. customthe filtrate is evaporated
  3. customThe residue is chromatographed on silica gel, elution
  4. customThe solid obtained
  5. customis crystallized from dichloromethane/heptane

Sources & evidence

ORD record
ord-b3bca0b74b5d430494a980ab9767bba5
Source dataset
uspto-grants-2013_02
Patent number
US08372879B2

Reaction notes

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