(4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol → 4-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone
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]=1Participants
4
Procedure
To a solution of (4-cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol from Step D (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 hrs. 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 that was sufficiently pure for use in the next step.