quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanol → quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanone

HRID 390361Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]([C:13]2[N:17]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[N:15][CH:14]=2)[OH:12])[CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2].O=[Mn]=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([C:13]2[N:17]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:16]=[N:15][CH:14]=2)=[O:12])[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 12) 3.7 g, 7.9 mmol) in CH2Cl2 (50 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (4.1 g, 47.4 mmol) at room temperature. The mixture was heated to 60° C. for 2 h. The mixture was then cooled to room temperature and filtered through celite and the solvent was removed under vacuum to get quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanone, (Intermediate 13) (3.6 g, 97%).

Workup

customat room temperature
temperatureThe mixture was then cooled to room temperature
filtrationfiltered through celite
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-665549a522b14cc78a45c5c1ccbe8dd0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383646B2

Reaction notes

Loading…