HCID 15124020, compound → HCID 15124021, compound

HRID 1084870Notes

Reaction equation

[CH3:1][C:2]1[C:6]2[C:7]([OH:22])=[C:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][C:3]=1C(O)=O>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:1][C:2]1[C:6]2[C:7]([OH:22])=[C:8]([C:18]([CH3:20])([CH3:19])[CH3:21])[CH:9]=[C:10]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])[C:5]=2[O:4][CH:3]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 3-methyl-4-hydroxy-5-tert-butyl-7-(2-thienoyl)-benzofuran-2-carboxylic acid (0.345 g, 0.96 mmol) in quinoline (1.0 mL) at room temperature was added fine copper powder (0.061 g, 0.96 mmol). The reaction mixture was flushed with nitrogen and heated in an oil bath to 200° C. until all CO2 evolution had ceased (about 20 min.). The reaction mixture was cooled to room temperature and poured into 30 mL 2N HCl. The aqueous solution was extrated with EtOAc (3×15 mL). The combined organic extracts were washed with 2N HCl (2×10 mL), water (10 mL) and saturated NaCl (10 mL) and dried over Na2SO4. Filtration, concentration and flash chromatography (85:15, hexane:EtOAc) afforded pure compound 14. 1H NMR d 1.5 (9H, s), 2.5 (3H, s), 5.74 (1H, s), 7.18 (1H, dd, J=4 Hz), 7.34 (1H, s), 7.68 (1H, d, J=4 Hz), 7.73 (1H, d, J=4 Hz), 7.74 (1H, s).

Workup

customThe reaction mixture was flushed with nitrogen
custom(about 20 min.)
temperatureThe reaction mixture was cooled to room temperature
additionpoured into 30 mL 2N HCl
washThe combined organic extracts were washed with 2N HCl (2×10 mL), water (10 mL) and saturated NaCl (10 mL)
dry with materialdried over Na2SO4
filtrationFiltration, concentration and flash chromatography (85:15, hexane:EtOAc)

Sources & evidence

ORD record: ord-ee34e5f9c88740dc8ee0c134429f4379
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006549

Reaction notes

Loading…