HCID 22018374, compound → HCID 178438793, compound

HRID 1368563Notes

Reaction equation

HRID 1368563 reaction equation
[CH2:1]([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)[CH:2]=[CH2:3]>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]([CH2:1][CH2:2][CH3:3])[CH:5]=3)[CH:10]=2)([OH:18])[CH:15]([CH3:17])[CH3:16])[N:20]=[CH:21]1

Participants

4

Reactant 1

HCID 22018374HCID 22018374, compound

Product 1

HCID 178438793HCID 178438793, compoundYield 162.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-(6-Allylnaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (1.40 g) was dissolved in THF-methanol (1:2) (15 ml). To the solution was added 10% palladium carbon (140 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. The residue was chromatographed on silica gel (eluent, hexane:THF=1:1) and crystallized from isopropyl ether-hexane to give the titled compound (1.28 g) as a colorless powder.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. customThe residue was chromatographed on silica gel (eluent, hexane:THF=1:1)
  5. customcrystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-f58e3c395ce64ec39709d92c8655885e
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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