Cyclohexane → HCID 66625415, compound

HRID 1946958Notes

Reaction equation

HRID 1946958 reaction equation
C(OP([CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)(=O)OCC)C.CC([O-])(C)C.[K+].[CH3:40][C:41]([CH3:51])([CH3:50])[C:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=O.C1CCCCC1>C1COCC1>[CH3:40][C:41]([CH3:51])([CH3:50])[C:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[CH:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 70308tert-Butyl phenyl ketoneHCID 2763175diethyl ((1-(triphenylmethyl)-1H-imidazol-4-yl)methyl)phosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66625415HCID 66625415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of (1-trityl-1H-imidazol-4-ylmethyl)-phosphonic acid diethyl ester (341 mg; CAS 473659-21-1) at r.t. in THF (7.5 ml) under an argon atmosphere was added potassium tert-butylate (83 mg). The mixture was then stirred at r.t. for 15 minutes, and 2,2-dimethylpropiophenone (0.1 ml) was added in one portion. The mixture (clear brown orange solution) was heated to 80° C. and stirring at that temperature was continued for 24 hours. The reaction mixture was directly adsorbed on silica gel. The product was isolated by chromatography (gradient: cyclohexane→cyclohexane/EtOAc 65:35) to give 4-(3,3-dimethyl-2-phenyl-but-1-enyl)-1-trityl-1H-imidazole (135 mg; not completely pure) as light yellow solid. MS (ISP): 243.2 ([Trt]+)

Workup

  1. temperatureThe mixture (clear brown orange solution) was heated to 80° C.
  2. stirringstirring at that temperature
  3. waitwas continued for 24 hours

Sources & evidence

ORD record
ord-ae2fb9c98d944f6480038a5322ffd056
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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