(4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol → 4-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone

HRID 2306215Notes

Reaction equation

HRID 2306215 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[N:12]=[CH:13][N:14]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=2)[OH:10])=[CH:5][C:4]=1[F:35])#[N:2]>C(Cl)Cl.O=[Mn]=O>[C:29]1([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:14]2[CH:15]=[C:11]([C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:35])[CH:5]=3)=[O:10])[N:12]=[CH:13]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 11134299(4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol

Product 1

HCID 545629854-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol, as described above in Step A, (10.0 g, 21.8 mmol) in CH2Cl2 (300 mL) was added MnO2 (18.9 g, 218 mmol) and the resulting mixture was heated to reflux for 18 hours. The mixture was allowed to cool, then filtered through a pad of celite, washing with CH2Cl2. The filtrate was concentrated under reduced pressure to provide the titled product as a white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 18 hours
  3. temperatureto cool
  4. filtrationfiltered through a pad of celite
  5. washwashing with CH2Cl2
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-561bee5747e049f2a51cd873dede433b
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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