HCID 22018351, compound → HCID 178438792, compound

HRID 1368564Notes

Reaction equation

HRID 1368564 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([C:19]1[N:20]=[CH:21][N:22](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:23]=1)([OH:18])[CH:15]([CH3:17])[CH3:16])[CH:8]=[CH:7]2)([CH3:3])=[CH2:2]>C1COCC1.CO.[C].[Pd]>[NH:22]1[CH:23]=[C:19]([C:14]([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=3)[CH:10]=2)([OH:18])[CH:15]([CH3:17])[CH3:16])[N:20]=[CH:21]1

Participants

4

Reactant 1

HCID 22018351HCID 22018351, compound

Product 1

HCID 178438792HCID 178438792, compoundYield 167.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-(6-Isopropenylnaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (1.70 g) was dissolved in THF-methanol (2:1) (12 ml). To the solution were added 10% palladium carbon (170 mg), and the mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The catalyst was filtered and washed with THF. The filtrate was concentrated and the obtained residue was purified by silica gel chromatography (eluent, hexane:THF=1:1). Crystallization from isopropyl ether-hexane gave the titled compound (1.60 g) as a colorless powder.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. customthe obtained residue was purified by silica gel chromatography (eluent, hexane:THF=1:1)
  5. customCrystallization from isopropyl ether-hexane

Sources & evidence

ORD record
ord-40523ffadffc498784c2c55186ffb2a6
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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