Sodium hydride → 4-[1-hydroxy-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile
Reaction equation
[H-].[Na+].[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][OH:28])[N:24]=[CH:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:29]1[CH2:31][CH:30]1[C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1>CN(C)C=O>[OH:29][CH:30]([C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1)[CH2:31][O:28][CH2:27][C:25]1[N:24]=[CH:23][N:22]([C:3]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:26]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
20.0 mmol of sodium hydride (60% dispersion in paraffin) are added to a solution of 20.0 mmol of (1-trityl-1H-imidazol-4-yl)methanol [33769-07-02] in 120 ml of absolute N,N-dimethylformamide under argon. The mixture is heated at 100° C. for 1 hour and then cooled to 40° C. A solution of 20.0 mmol of 4-oxiranylbenzonitrile [52695-39-3] in 10 ml of absolute N,N-dimethylformamide is added dropwise at 35-40° C., and the reaction mixture is stirred at 40° C. for 15 minutes. The reaction mixture is cooled to room temperature, poured into ice-water and extracted with ethyl acetate. The combined organic phases are washed with water and brine, dried over sodium sulphate and evaporated. The title compound is obtained as a white solid from the residue by flash chromatography (SiO2 60 F). Rf=0.29 (dichloromethane-methanol 95:5); Rt=4.26 (gradient I).
Workup
- temperaturecooled to 40° C
- temperatureThe reaction mixture is cooled to room temperature
- extractionextracted with ethyl acetate
- washThe combined organic phases are washed with water and brine
- dry with materialdried over sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-2dc2068d57674b51af69889938be7bd0
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138176B2
Reaction notes
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