Sodium Hydroxide → 5-Cyano-1-benzothiophene-7-carboxylic acid
Reaktionsgleichung
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[C:6]2[S:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)#[N:2].[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6]2[S:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)#[N:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Ethyl 5-cyano-1-benzothiophene-7-carboxylate (5.6 g, 24.3 mmol) was dissolved THF (96 mL) and to the resultant solution was added an aqueous solution of NaOH (1.07 g of NaOH in 14 mL of water, 26.7 mmol) at 0° C. The mixture was stirred at room temperature overnight and then most of the solvent was removed by evaporation. The residue was dissolved in an aqueous solution of NaOH (0.1 M). The solution was washed thrice with chloroform, acidified with 2M HCl and then extracted with ethyl acetate. The organic solution was separated and the solvent was evaporated. The residue was flash chromatographed on silica gel (CH2Cl2-MeOH—NH4OH, 8:2:0.5). There was obtained 4.3 g (85%) of 5-cyano-1-benzothiophene-7-carboxylic acid as a tan solid. 1H NMR (500 MHz, DMSO-d6): 7.7 (d, 1H), 8.1 (d, 2H), 8.3 (d, 1H), 8.7 (s, 1H), 14 (b, 1H); LCMS: m/z 202 (M−1)−.
Aufarbeitung
- custommost of the solvent was removed by evaporation
- dissolutionThe residue was dissolved in an aqueous solution of NaOH (0.1 M)
- washThe solution was washed thrice with chloroform
- extractionextracted with ethyl acetate
- customThe organic solution was separated
- customthe solvent was evaporated
- customchromatographed on silica gel (CH2Cl2-MeOH—NH4OH, 8:2:0.5)
Quellen und Nachweise
- ORD-Eintrag
- ord-a950e7cc4e5c48dd80367ff413ef359b
- Quelldatensatz
- uspto-grants-2008_07
- Patentnummer
- US07402581B2
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