Isobutyrophenone → 4-(3-methyl-2-phenyl-but-1-enyl)-1-trityl-1H-imidazole

HRID 1946955Notes

Reaction equation

HRID 1946955 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+].[C:40]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=O)[CH:41]([CH3:43])[CH3:42]>C1COCC1>[CH3:42][CH:41]([CH3:43])[C:40]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[CH:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 69144IsobutyrophenoneHCID 2763175diethyl ((1-(triphenylmethyl)-1H-imidazol-4-yl)methyl)phosphonateHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of (1-trityl-1H-imidazol-4-ylmethyl)-phosphonic acid diethyl ester (921 mg; CAS 473659-21-1) at r.t. in THF (20 ml) under an argon atmosphere was added potassium tert-butylate (241 mg). The mixture was then stirred at r.t. for 15 minutes, and isobutyrophenone (0.25 ml) was added in one portion. The mixture (clear brown orange solution) was heated to 80° C. for 21 hours. The reaction mixture was filtered and the cake was washed with EtOAc. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1) to give 4-(3-methyl-2-phenyl-but-1-enyl)-1-trityl-1H-imidazole (91 mg; not completely pure) as orange sticky solid. MS (ISP): 243.2 ([Trt]+)

Workup

  1. temperatureThe mixture (clear brown orange solution) was heated to 80° C. for 21 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe cake was washed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-ee3fef3ee47c4762a8af6abe24a927d3
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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