Dichloromethane → HCID 178442467, compound

HRID 1946959Notes

Reaction equation

HRID 1946959 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[C:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:4][C:5]1[N:6]=[CH:7][N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1.ClCCl>CO.[Pd]>[CH3:1][C:2]([CH3:36])([CH3:35])[CH:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:4][C:5]1[N:6]=[CH:7][NH:8][CH:9]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 66625415HCID 66625415, compound

Product 1

HCID 178442467HCID 178442467, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(3,3-dimethyl-2-phenyl-but-1-enyl)-1-trityl-1H-imidazole (121 mg) at r.t. in methanol (5 ml) and dichloromethane (1 ml) under an argon atmosphere was added 10% Pd/C (12 mg). The mixture was stirred under a hydrogen atmosphere (balloon) 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-(3,3-dimethyl-2-phenyl-butyl)-1H-imidazole (25 mg) as colorless gum. MS (ISP): 229.4 ([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; gradient: CH2Cl2→CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-fde458a8f8be40ccb225800b06248aa5
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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