Water → HCID 59547225, compound

To a solution of methyl 5-methylselenophene-2-carboxylate (5.0 g, 24.6 mmol) in acetic acid (30 mL) was added selenium dioxide (10.84 g, 98.4 mmol) at rt and the mixture was refluxed for 8 h. The cooled reaction mixture was poured into ice cooled water and stirred for 15 min. The solution was extracted with chloroform (3×100 mL) and the combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtOAc (9:1) as eluents to give the product as pale yellow color solid (4.0 g, 75%), mp 63-65° C.; 1H NMR (400 MHz, CDCl3): δ 9.84 (1H, s, —CHO), 8.11 (1H, d, J=4.0 Hz, H-3), 7.99 (1H, d, J=4.0 Hz, H-4), 3.92 (3H, s, —COOCH3).

1. temperaturethe mixture was refluxed for 8 h
2. customThe cooled reaction mixture
3. additionwas poured into ice
4. extractionThe solution was extracted with chloroform (3×100 mL)
5. washthe combined organic layer was washed with water, brine
6. dry with materialdried over sodium sulfate
7. filtrationThe solution was filtered
8. customevaporated the solvent
9. customThe residue was chromatographed over silica gel column

ORD record

ord-91cbfbbdf4ef43d8bf814de25de50a81

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143237B2