Potassium Hydroxide → 5-Diallylaminomethyl-thiophene-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][N:11]([CH2:15][CH:16]=[CH2:17])[CH2:12][CH:13]=[CH2:14])=[CH:8][CH:9]=1)=[O:4].[OH-].[K+]>CO>[CH2:12]([N:11]([CH2:10][C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)[CH2:15][CH:16]=[CH2:17])[CH:13]=[CH2:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 4.5 g (17.9 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid methyl ester in 45 ml methanol were added to 17.9 ml of a 1 N aqueous solution of KOH (17.9 mmol). The reaction mixture was stirred at 50° C. for 16 h and 1 h at reflux. The solvent was evaporated, 20 ml water was added to the residue and 9 ml of a 2 N aqueous solution of HCl. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate) to yield 4.05 g (17.06 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid; exact MW [M+H] calc'd: 238.09; MW found [M+H]: 238.3.
Workup
- temperatureat reflux
- customThe solvent was evaporated
- addition20 ml water was added to the residue and 9 ml of a 2 N aqueous solution of HCl
- extractionThe aqueous phase was extracted with ethyl acetate
- dry with materialthe combined organic phases were dried over Na2SO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-b17ff0364e5a47e0aa4d2f4b50d032a6
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098247B2
Reaction notes
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