1-Phenyl-1-propanone → HCID 66625783, compound

HRID 1946953Notes

Reaction equation

HRID 1946953 reaction equation
C(OP(CC1[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.[CH3:34][C:35]([O-])(C)C.[K+].[C:40]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=O)[CH2:41][CH3:42]>C1COCC1.C(OCC)(=O)C>[C:44]1([C:40]([CH2:34][CH3:35])=[CH:41][C:42]2[N:11]=[CH:12][N:13]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:14]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 2763175diethyl ((1-(triphenylmethyl)-1H-imidazol-4-yl)methyl)phosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66625783HCID 66625783, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (1-trityl-1H-imidazol-4-ylmethyl)-phosphonic acid diethyl ester (1.24 g; CAS 473659-21-1) at room temperature (r.t.) in THF (20 ml) under an argon atmosphere was added potassium tert-butylate (301 mg). After 15 minutes stirring at room temperature, propiophenone (0.3 ml) was added in one portion. The mixture was heated to 80° C. and stirring at that temperature was continued for 2 days. The compact suspension was cooled to r.t. and the solid was filtered off and washed with THF. The filtrate was concentrated to leave a dark violet viscous oil. This was taken up in ethyl acetate (EtOAc) and washed with brine. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient cyclohexane→cyclohexane/EtOAc 3:2) to give 4-(2-phenyl-but-1-enyl)-1-trityl-1H-imidazole (269 mg; not completely pure) as an off-white solid. MS (ISP): 243.2 ([Trt]+)

Workup

  1. temperatureThe mixture was heated to 80° C.
  2. stirringstirring at that temperature
  3. waitwas continued for 2 days
  4. temperatureThe compact suspension was cooled to r.t.
  5. filtrationthe solid was filtered off
  6. washwashed with THF
  7. concentrationThe filtrate was concentrated
  8. customto leave a dark violet viscous oil
  9. washwashed with brine
  10. extractionThe aqueous phase was back extracted with EtOAc
  11. washThe combined organics were washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe crude product was purified by column chromatography (silica gel; gradient cyclohexane→cyclohexane/EtOAc 3:2)

Sources & evidence

ORD record
ord-9610251b7ea44607a0f311605ab5e231
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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