Tetrahydrofuran → HCID 68663956, compound

HRID 452776Notes

Reaction equation

HRID 452776 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[C:15]([C:18]4[O:19][C:20]([CH3:23])=[N:21][N:22]=4)[CH:16]=[CH:17][C:12]=3[O:11][CH:10]=2)=[CH:5][CH:4]=1.O1CCCC1.[H][H]>[C].[Pd].CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:13]3[CH:14]=[C:15]([C:18]4[O:19][C:20]([CH3:23])=[N:21][N:22]=4)[CH:16]=[CH:17][C:12]=3[O:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 68663586HCID 68663586, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68663956HCID 68663956, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-[3-(4-methoxyphenyl)-1-benzofuran-5-yl]-5-methyl-1,3,4-oxadiazole (447 mg, 1.46 mmol), 10% palladium carbon (50% containing water, 450 mg), tetrahydrofuran (5 mL) and methanol (15 mL) was stirred at room temperature for 48 hr under 1 atm hydrogen atmosphere. Palladium on carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate), and crystallized from hexane/ethyl acetate to give the title compound (335 mg, yield 74%) as colorless crystals.

Workup

  1. customPalladium on carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)
  4. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c12f8792ab3d42cdbe8c7539831c8b01
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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