Hydrochloric Acid → (1-Oxo-indan-2-yl)-acetic acid
Reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH:3]2[CH2:7][CH:8]3[C:13]([CH:12]=[CH:11][CH:10]=[CH:9]3)=[C:2]12.[OH-].[Na+].I([O-])(=O)(=O)=[O:17].[Na+].Cl>O.O.[Ru](Cl)(Cl)Cl.C(O)(C)C>[O:17]=[C:2]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:3]1[CH2:4][C:5]([OH:1])=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of Tetrahydroindeno[1,2-b]furan-2-one (Example I5 or commercially available, 0.200 g, 1.15 mmol) in water (20 mL) was added sodium hydroxide (0.051 g, 1.26 mmol) and the solution was heated to 100° C. for one hour. The solution was cooled down to rt and Ruthenium(III) chloride hydrate (0.048 g, 0.230 mmol) was added followed by sodium periodate (0.368 mg, 1.72 mmol) in water (5 mL) dropwise. The solution was stirred at rt for 1 h and isopropanol was added (0.2 mL). The pH was acidified to 1 using 2M HCl and the reaction was filtered. The filtrate was extracted with dichloromethane (3*30 mL) and the combined organic layers were washed with water (30 mL), dried and concentrated to give (1-Oxo-indan-2-yl)-acetic acid (Pale yellow solid, 170 mg, 78%). C11H10O3; MW: 190.2. LCMS (method A) RT 1.16 min; ES− 189 (35%, MH+), 175 (70%), 145 (100%), 127 (90%). 1H NMR (400 MHz, CD3OD) δ 7.71 (1H, d), 7.65 (1H, t), 7.54 (1H, d), 7.41 (1H, t), 3.39-3.51 (1H, m), 2.83-3.02 (3H, m), 2.70 (1H, m) ppm.
Workup
- temperatureThe solution was cooled down to rt
- filtrationthe reaction was filtered
- extractionThe filtrate was extracted with dichloromethane (3*30 mL)
- washthe combined organic layers were washed with water (30 mL)
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d857139b3a0b422486d39447e354ad03
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946280B2
Reaction notes
Loading…