HCID 21194440, compound → HCID 21194195, compound

In 30 ml of acetone was dissolved 0.70 g (3.00 mmols) of ethyl 4-hydroxymethyl-1-methyl-2-indolecarboxylate. After 3.3 ml of Jones' reagent, which was prepared by dissolving 26.7 g of chromium (VI) oxide in a mixture of 23 ml of conc. sulfuric acid and 40 ml of water and adding water to make the whole volume 100 ml, was added dropwise to the above solution at room temperature, the mixture was stirred at room temperature for an hour. The reaction mixture was poured onto ice water and the aqueous layer was extracted three times with chloroform. The combined extracts were washed with saturated sodium hydrogencarbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 0.38 g (51.2%) of ethyl 4-carboxy-1-methyl-2-indolecarboxylate.

1. additionwas added dropwise to the above solution at room temperature
2. additionThe reaction mixture was poured onto ice water
3. extractionthe aqueous layer was extracted three times with chloroform
4. washThe combined extracts were washed with saturated sodium hydrogencarbonate solution
5. dry with materialAfter drying over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-3fbc40ca1453460db25905b51e16bba3

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248772B1