HCID 67024288, compound → HCID 136348329, compound

HRID 384098Notes

Reaction equation

HRID 384098 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([O:20][CH2:21][O:22][CH3:23])[CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.O1CCCC1.[C].[Pd]>[CH3:23][O:22][CH2:21][O:20][C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[O:19][N:18]=1

Participants

5

Reactant 1

HCID 67024288HCID 67024288, compound

Product 1

HCID 136348329HCID 136348329, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 5-(4-(benzyloxy)phenyl)-3-(methoxymethoxy)isoxazole (1.44 g) in methanol (15 ml) and tetrahydrofuran (15 ml), 200 mg of 10% palladium-carbon catalyst was added, and the reaction solution was stirred overnight at room temperature under hydrogen atmosphere. The reaction solution was filtered through Celite, the solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-50:50)) to afford the title compound as a pale yellow solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue obtained
  4. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (10:90-50:50))

Sources & evidence

ORD record
ord-8363e738f5d2410fb82a568f17120bc4
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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