2-Chloro-5-phenyl-thiophene-3-carboxylic acid ethyl ester → 2-Chloro-5-phenylthiophene-3-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[Cl:17])=[O:5])C>[OH-].[Na+].C(O)C>[Cl:17][C:7]1[S:8][C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:10][C:6]=1[C:4]([OH:5])=[O:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
2-Chloro-5-phenyl-thiophene-3-carboxylic acid ethyl ester (0.44 g, 1.65 mmol) was dissolved in a solution of 1 M NaOH (3 mL) and ethanol (2 mL). The reaction mixture was heated to 100° C. using microwave irradiation for 10 minutes. After cooling, the reaction mixture was partitioned between diethyl ether and water. The aqueous solution was acidified with 1 M HCl and further extracted with diethyl ether. The combined organic solutions were dried over magnesium sulfate, filtered and the solvent evaporated. The residue was triturated in diethyl ether and filtered to give the title compound (0.17 g). 1H NMR (400 MHz, CHCl3-d): δ 7.6 (s, 1H), 7.55 (d, 2H), 7.4-7.3 (m, 3H).
Workup
- custommicrowave irradiation for 10 minutes
- temperatureAfter cooling
- customthe reaction mixture was partitioned between diethyl ether and water
- extractionfurther extracted with diethyl ether
- dry with materialThe combined organic solutions were dried over magnesium sulfate
- filtrationfiltered
- customthe solvent evaporated
- customThe residue was triturated in diethyl ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-d065559b7a884d1db642ceaa38a97027
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614209B2
Reaction notes
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