1,4-Dioxane → HCID 136338827, compound

HRID 503001Notes

Reaction equation

HRID 503001 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([CH:20]3[CH2:22][CH2:21]3)[C:18]([C:23]3([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)=[N:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.O1CCOCC1>CO.[OH-].[Pd+2].[OH-]>[CH:20]1([N:19]2[C:18]([C:23]3([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)[CH2:24][CH2:25][CH2:26]3)=[N:17][N:16]=[C:15]2[C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 68469387HCID 68469387, compound

Product 1

HCID 136338827HCID 136338827, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

3-[4-(Benzyloxy)phenyl]-4-cyclopropyl-5-[1-(2-thienyl)cyclobutyl]-4H-1,2,4-triazole was dissolved in methanol (4 ml) and 1,4-dioxane (3 ml) and, after palladium hydroxide (236 mg) was added thereto, the whole was stirred under a hydrogen atmosphere of 1 atm at room temperature for 15 hours. After filtration through celite, the filtrate was purified by silica gel chromatography (chloroform:methanol=99:1 to 95:5) and the resulting crystals were washed with diisopropyl ether to obtain 32 mg of 4-{4-cyclopropyl-5-[1-(2-thienyl)cyclobutyl]-4H-1,2,4-triazol-3-yl}phenol (white crystals).

Workup

  1. filtrationAfter filtration through celite
  2. customthe filtrate was purified by silica gel chromatography (chloroform:methanol=99:1 to 95:5)
  3. washthe resulting crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-b1ff4558ede043e98217198a5d5581d2
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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