Hydrochloric Acid → 3-(Furan-2-yl)-2-oxopropanoic acid
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](=[O:11])[C:8]([O-:10])=[O:9].[OH-].[Na+].Cl>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](=[O:11])[C:8]([OH:10])=[O:9]Participants
4
Conditions
- Temperature
- 90 °C
Procedure
To a 100 mL flask, 3-(furan-2-yl)-2-oxopropanoate (940 mg) along with 23 mL cold 6N NaOH was added. The insoluble mixture was stirred in a 90° C. bath for 5 min until dissolved. Cold 1N HCl was added until solution was acidic (approx 120 mL). Solution was extracted 2×50 mL EtOAc. Combined organic layers were washed with 40 mL brine and dried with Na2SO4. Solution was evaporated to yield 540 mg brown solid. Solid was further purified by reversed-phase high-performance liquid chromatography (HPLC) ramping from 97% aqueous trifluoroacetic acid (TFA) to acetonitrile (ACN).