Hydrochloric Acid → 1-[(1-Ethoxyethyl)-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-1H-imidazol-2-yl]ethanol
Reaction equation
[CH2:1]([O:3][CH:4]([N:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[C:9]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[N:8]=[C:7]1[C:26](=[O:28])[CH3:27])[CH3:5])[CH3:2].[BH4-].[Na+].Cl.[Cl-].[Na+]>>[CH2:1]([O:3][CH:4]([N:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=2)=[C:9]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[N:8]=[C:7]1[CH:26]([OH:28])[CH3:27])[CH3:5])[CH3:2]Participants
Reactant 4
Product 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-[(1-ethoxyethyl)-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl)-1H-imidazol-2-yl]ethanone (Step 1) (1.08 g.; 2.9 mmol) at 25° C. was added sodium borohydride (109.7 mg; 2.9 mmol). After stirring for 20 hours, the reaction mixture was cooled to 0° C. and 50 ml of a 1% aqueous solution of hydrochloric acid was added. This solution was saturated with solid sodium chloride and extracted with 100 ml, then 2×50 ml of methylene chloride. The organics were combined then washed with 50 ml of a saturated, aqueous solution of sodium bicarbonate. The organic extracts were dried (MgSO4), filtered and evaporated under reduced pressure to provide 1.06 g of a light yellow foam, which was purified by flash chromatography (SiO2, 75% ethyl acetate/hexane) to provide 907 mg of the desired protected alcohol.
Workup
- extractionextracted with 100 ml
- washThe organics were combined then washed with 50 ml of a saturated, aqueous solution of sodium bicarbonate
- dry with materialThe organic extracts were dried (MgSO4)
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-5a7da9c0302c435baa9865bf60885e0e
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06426360B1
Reaction notes
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