Dichloromethane → 4-(3-methyl-2-phenyl-butyl)-1-trityl-1H-imidazole

HRID 1946956Notes

Reaction equation

HRID 1946956 reaction equation
[CH3:1][CH:2]([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:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1.C(Cl)Cl>CO.[Pd]>[CH3:1][CH:2]([CH3:35])[CH:3]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 666257944-(3-methyl-2-phenyl-but-1-enyl)-1-trityl-1H-imidazole

Product 1

HCID 597427414-(3-methyl-2-phenyl-butyl)-1-trityl-1H-imidazoleYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(3-methyl-2-phenyl-but-1-enyl)-1-trityl-1H-imidazole (87 mg) at r.t. in methanol (4 ml) and CH2Cl2 (1 ml) under an argon atmosphere was added the 10% Pd/C (10 mg). The mixture was then stirred at r.t. under a hydrogen atmosphere for 38 hours. The catalyst was filtered off and washed with MeOH. The filtrate was concentrated to leave 4-(3-methyl-2-phenyl-butyl)-1-trityl-1H-imidazole (82 mg) of an off-white sticky solid which was used in the next step without further purification. MS (ISP): 243.2 ([Trt]+)

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-da0cef515c3644968c9d19e5f6e4d8e7
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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