Water → 4-(4-Chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:22][C:23]=2[CH2:24][CH2:25][C:26](O)=[O:27])=[CH:15][CH:14]=1.O>C(OCC)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:22][C:23]=2[CH2:24][CH2:25][CH2:26][OH:27])=[CH:17][CH:18]=1Participants
Procedure
Lithium aluminium hydride (185 mg) was gradually added to a tetrahydrofuran (20 ml) solution of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionic acid (1.47 g) at room temperature. After the mixture was stirred for 1 hour, water (2 ml) was added to the reaction mixture with cooling with ice, and stirred for further 30 minutes. Diethyl ether (50 ml) was added to the reaction mixture, which was then dried (MgSO4), and the insoluble substances were removed by filtration. The resulting filtrate was concentrated, and the crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropanol (435 mg, 31%). This was recrystallized from dichloromethane-isopropyl ether to give colorless prisms. mp 128-129° C.
Workup
- temperaturewith cooling with ice
- stirringstirred for further 30 minutes
- dry with materialwas then dried (MgSO4)
- customthe insoluble substances were removed by filtration
- concentrationThe resulting filtrate was concentrated
- customthe crystals thus precipitated
- filtrationwere collected by filtration
Sources & evidence
- ORD record
- ord-6eb4c5d0d53040a689172ef512b6a2db
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498179B1
Reaction notes
Loading…