Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-Chloro-2-[4-hydroxy-1-(3-thienyl)butoxy]benzonitrile
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:11]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH2:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:11]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH2:12][CH2:13][CH2:14][OH:15])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
The product from step (c) (1.12 g, 2.65 mmol) was dissolved in ethanol (60 ml) and pyridinium p-toluenesulphonate (0.067 g, 0.27 mmol) added. The reaction was heated to 55° C. and stirred for 18 h. The reaction was cooled and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (180 ml) and the organic layer washed with aqueous saturated sodium bicarbonate solution (2×30 ml), water (2×30 ml) and brine (20 ml). After drying over magnesium sulphate, the solution was evaporated in vacuo to give the title compound as a colourless oil (0.72 g, 88%).
Workup
- temperatureThe reaction was cooled
- customthe solvent removed in vacuo
- dissolutionThe residue was dissolved in ethyl acetate (180 ml)
- washthe organic layer washed with aqueous saturated sodium bicarbonate solution (2×30 ml), water (2×30 ml) and brine (20 ml)
- dry with materialAfter drying over magnesium sulphate
- customthe solution was evaporated in vacuo
Sources & evidence
- ORD record
- ord-adb01c8cdac447a2bd8992625b596786
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743939B2
Reaction notes
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