HCID 57577342, compound → HCID 57577327, compound

HRID 420768Notes

Reaction equation

HRID 420768 reaction equation
C([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]2[CH2:18][CH2:17][O:16][CH2:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[O:16]1[CH2:17][CH2:18][CH:14]([O:13][C:12]2[CH:19]=[CH:20][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:15]1

Participants

4

Reactant 1

HCID 57577342HCID 57577342, compound

Product 1

HCID 57577327HCID 57577327, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Benzyloxy-phenoxy)-tetrahydro-furan (1.80 g, 6.66 mmol) was dissolved in 30 ml ethyl acetate and stirred with 200 mg Pd/C 10% under hydrogen atmosphere for 16 hours. The catalyst was filtered off and the solvent evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→20:80 gradient). The desired compound was obtained as a light brown solid (900 mg, 75%) MS (m/e): 179.1 (M−H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→20:80 gradient)

Sources & evidence

ORD record
ord-4f3b3eca9b14446384ba97bd91a6f1b5
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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