Acetic Acid → 4-[1-hydroxy-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile
Reaction equation
[BH4-].[Na+].[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][O:28][CH2:29][C:30]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)=[O:31])[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.C(O)(=O)C>C(O)C>[OH:31][CH:30]([C:32]1[CH:33]=[CH:34][C:35]([C:36]#[N:37])=[CH:38][CH:39]=1)[CH2:29][O:28][CH2:27][C:25]1[N:24]=[CH:23][N:22]([C:3]([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)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:26]=1Participants
5
Procedure
Sodium borohydride is added in portions to a solution of 1 mmol of 4-[2-(1-trityl-1H-imidazol-4-ylmethoxy)acetyl]benzonitrile in 12 ml of ethanol at 0° C. The reaction solution is stirred at room temperature for 12 hours, then poured into ice-water and stirred for 15 minutes. The mixture is adjusted to pH 5 by adding glacial acetic acid and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60 F).
Workup
- stirringstirred for 15 minutes
- extractionextracted with tert-butyl methyl ether (2×)
- washThe combined organic phases are washed with water and brine
- dry with materialdried over sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-d31542b71415400089a13b2101c9ca79
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138176B2
Reaction notes
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