Methanol → Methyl 3-oxo-2,3-dihydro-1H-indene-5-carboxylate

Temperature

0 °C

3-Oxo-2,3-dihydro-1H-indene-5-carboxylic acid (16.0 g, 90.909 mmol, 1.0 eq.) was dissolved in MeOH (140 ml) and cooled to 0° C.; sulfuric acid (4.5 ml) was added and the mixture was refluxed for 4 hours. The solvent was concentrated under reduced pressure, and the residue was taken up in water, rendered basic with sat. sodium hydrogen carbonate solution (200 ml) and extracted with ethyl acetate (2×400 ml). The combined org. phases were washed with water and sat. NaCl solution (in each case 2×200 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 15% ethyl acetate in hexane). Yield: 58% (10.0 g, 52.63 mmol)

1. temperaturethe mixture was refluxed for 4 hours
2. concentrationThe solvent was concentrated under reduced pressure
3. extractionextracted with ethyl acetate (2×400 ml)
4. washphases were washed with water and sat. NaCl solution (in each case 2×200 ml),
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. custompurified by column chromatography (silica gel, 15% ethyl acetate in hexane)

ORD record

ord-8d58f295f9c24909b7c886f2e3e09114

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680159B2