Ethyl Acetate → 5-(3-Benzyloxy-phenoxy)-thiophene-2-carbonitrile
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([C:19]1[S:23][C:22]([C:24]#[N:25])=[CH:21][CH:20]=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][C:19]1[S:23][C:22]([C:24]#[N:25])=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of the resulting 3-benzyloxy-phenol (2.6 g, 13.0 mmol) and a 5-nitrothiophene-2-carbonitrile (2.0 g, 13.0 mmol) in dimethylsulfoxide (25 mL) was added potassium carbonate (1.98 g, 14.0 mmol), and the solution was stirred at 70° C. for 3 hours. The reaction solution was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and 5-(3-benzyloxy-phenoxy)-thiophene-2-carbonitrile (110 mg, 2.8%) was obtained as a pale brown solid.
Workup
- customwas allowed to room temperature
- customfor partitioning
- washthe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated
- customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-7a9418f9034c4cef895cad33acd521aa
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932272B2
Reaction notes
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