Ethanol → HCID 178471114, compound

HRID 350170Notes

Reaction equation

HRID 350170 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:53])=[C:9]([CH2:11][O:12][C:13]2[CH:52]=[CH:51][C:16]([CH2:17][N:18]3[CH:22]=[C:21](/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:30]CC4C=CC(OCC5N=C(C6OC=CC=6)OC=5C)=CC=4)=[N:19]3)=[CH:15][CH:14]=2)[N:10]=1.C(O)C>[C].[Pd].O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:53])=[C:9]([CH2:11][O:12][C:13]2[CH:52]=[CH:51][C:16]([CH2:17][N:18]3[CH:22]=[C:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([OH:30])=[N:19]3)=[CH:15][CH:14]=2)[N:10]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 69420190HCID 69420190, compound

Product 1

HCID 178471114HCID 178471114, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(E)-3-[1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxy]-1H-pyrazol-4-yl]propenoate (12.5 g), 5% palladium-carbon (20.0 g), ethanol (200 ml), and tetrahydrofuran (200 ml) was stirred under a hydrogen atmosphere at room temperature for 7 hours. After removal of the catalyst by filtration, the filtrate was concentrated. The obtained crystals were collected by filtration, and ethyl 3-[1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-3-hydroxy-1H-pyrazol-4-yl]propionate (4.40 g, yield: 56%) was obtained. This was recrystallized from tetrahydrofuran-hexane. Melting point: 145–146° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated
  4. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-cc07c1972f744535b1b2dccfb0d49b1a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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