Dichloromethane → HCID 178441354, compound

HRID 1946954Notes

Reaction equation

HRID 1946954 reaction equation
[C:1]1([C:7]([CH2:33][CH3:34])=[CH:8][C:9]2[N:10]=[CH:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl>CO.[Pd]>[C:1]1([CH:7]([CH2:33][CH3:34])[CH2:8][C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 66625783HCID 66625783, compound

Product 1

HCID 178441354HCID 178441354, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(2-phenyl-but-1-enyl)-1-trityl-1H-imidazole (260 mg) at r.t. in methanol (5 ml) and dichloromethane (2 ml) under an argon atmosphere was added 10% Pd/C (26 mg). The mixture was then stirred at r.t. under a hydrogen atmosphere for 17 hours. The catalyst was filtered off and washed with methanol. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 9:1 to give 4-(2-phenyl-butyl)-1H-imidazole (18 mg) as colorless gum. MS (ISP): 201.3 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (silica gel

Sources & evidence

ORD record
ord-5cc3bb1a69ef411ea4f2e18598c53c4c
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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