Hydrochloric Acid → 3-(3-Fluorophenyl)-7-methoxychromen-4-one

HRID 1455029Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[OH:19])=[O:10])[CH:5]=[CH:6][CH:7]=1.N1CCCC[CH2:21]1.C(OC(OCC)OCC)C.Cl>N1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:10])[C:11]3[C:12](=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[O:19][CH:21]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-(3-Fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone (1.76 g) was dissolved in pyridine (88 ml). Piperidine (8.8 ml) and triethylorthoformate (88 ml) were added and the mixture was stirred at 120° C. for 3.5 hours. After pouring the mixture into water and acidification with conc. HCl the crude product was filtered. Purification by column chromatography using heptane-ethyl acetate (7:3) as an eluant afforded 3-(3-fluorophenyl)-7-methoxychromen-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.57 (s, 1H), 8.06 (d, 1H, J 8.9 Hz), 7.45-7.50 (m, 3H), 7.21-7.25 (m, 1H), 7.20 (d, 1H, J 2.4 Hz), 7.12 (dd, 1H, J 8.9, 2.4 Hz), 3.92 (s, 3H).

Workup

filtrationwas filtered
customPurification by column chromatography

Sources & evidence

ORD record: ord-646b48680e1c461e8bba94a2f58f7dcf
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482340B2

Reaction notes

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