Ethanol → HCID 178469748, compound

HRID 350204Notes

Reaction equation

HRID 350204 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:53]=[CH:52][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:22]([O:30]CC3C=CC(OCC4N=C(C5C=CC=CC=5)OC=4C)=CC=3)=[N:21]2)=[CH:17][CH:16]=1.C(O)C>[C].[Pd].O1CCCC1>[OH:30][C:22]1[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:24][N:20]([CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:53][CH:52]=2)[N:21]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 23024781HCID 23024781, compound

Product 1

HCID 178469748HCID 178469748, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxy]-1H-pyrazol-4-carboxylate (2.84 g), 5% palladium-carbon (5.00 g), ethanol (25 ml), and tetrahydrofuran (25 ml) was stirred under a hydrogen atmosphere at room temperature for 4 hours. After removal oh the catalyst by filtration, the filtrate was concentrated. The obtained crystals were collected by filtration, and ethyl 3-hydroxy-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-carboxylate (968 mg, yield: 56%) was obtained. This was recrystallized from tetrahydrofuran-hexane. Melting point: 152–153° C.

Workup

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

Sources & evidence

ORD record
ord-f25314aed52245989a5b1914723682ed
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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