Pyridine → HCID 11641654, compound

HRID 1444791Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:26])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][O:23][CH3:24])=[CH:18][CH:17]=[C:16]([OH:25])[CH:15]=2.N1C=CC=CC=1.[O:33](S(C(F)(F)F)(=O)=O)[S:34]([C:37]([F:40])([F:39])[F:38])(=O)=[O:35].C(OCC)(=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:26])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][O:23][CH3:24])=[CH:18][CH:17]=[C:16]([O:25][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:35])=[O:33])[CH:15]=2

Participants

Conditions

Temperature: 0 °C

Procedure

3-(2,4-Dimethoxy-phenyl)-7-hydroxy-4-(2-methoxy-ethyl)-chromen-2-one (1.8 g, 5.2 mmol) and pyridine (30 mL) were dissolved in CH2Cl2 (200 mL) at room temperature and the reaction mixture was cooled to 0° C., then treated with Tf2O (1.3 mL). After 1 hour, ethyl acetate (200 mL) was poured into the reaction mixture and the reaction mixture was transferred into a separation funnel. The reaction mixture was then washed with 5% sodium bicarbonate (2×250 ml), water (250 ml) and then brine. The organic layer was dried over sodium sulfate and concentrated. Flash column chromatography on silica gel eluted with 20-50% ethyl acetate in hexane yielded the title compound as a yellow solid.

Workup

customthe reaction mixture was transferred into a separation funnel
washThe reaction mixture was then washed with 5% sodium bicarbonate (2×250 ml), water (250 ml)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated
washFlash column chromatography on silica gel eluted with 20-50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-915006dc6abd432486209baf1213b968
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662975B2

Reaction notes

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