Potassium Hydroxide → 2-[trans-3-(3-Carboxy-3,3-dimethylpropyloxy)styryl]-4-isopropylthiazole
Reaction equation
[CH3:1][C:2]([CH3:27])([C:22]([O:24]CC)=[O:23])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1.[OH-].[K+]>C(O)C.CO.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[C:22]([C:2]([CH3:27])([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[C:14]([CH:16]([CH3:17])[CH3:18])[N:15]=1)([OH:24])=[O:23]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 200 mg of 2-[trans-3-(3,3-dimethyl-3-ethoxycarbonylpropyloxy)styryl]-4-isopropylthiazole dissolved in 5 ml of ethanol were added 2 ml of 10% aqueous potassium hydroxide solution and three drops of 40% benzyltrimethylammonium hydroxide methanol solution, and the mixture was refluxed for 1 hour to effect hydrolysis of the ester. After completion of the reaction, ethanol was evaporated under reduced pressure and the residue was adjusted to pH 1-2 with addition of 10% hydrochloric acid and then extracted with ethyl ether. After drying of anhydrous magnesium sulfate, the solvent was evaporated and the solid formed was recrystallized from methanol to give 123 mg (yield 66%) of the title compound.
Workup
- temperaturethe mixture was refluxed for 1 hour
- customwas evaporated under reduced pressure
- additionthe residue was adjusted to pH 1-2 with addition of 10% hydrochloric acid
- extractionextracted with ethyl ether
- dry with materialAfter drying of anhydrous magnesium sulfate
- customthe solvent was evaporated
- customthe solid formed
- customwas recrystallized from methanol
Sources & evidence
- ORD record
- ord-b01298d2f61f4bfc8091e8fc4020f061
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04902700
Reaction notes
Loading…