2-Acetylhydroquinone → 2-(3,5-Difluorophenyl)-6-hydroxychroman-4-one

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1.OC1C=CC(O)=CC=1C(=O)C.[F:31]C1C=C(C=C(F)C=1)C=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[C:6]([F:31])[CH:7]=1

Komponenten

Edukt 3

HCID 102792-Acetylhydroquinone

HCID 5881603,5-Difluorobenzaldehyde

HCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Produkt 1

HCID 179784642-(3,5-Difluorophenyl)-6-hydroxychroman-4-one

Versuchsvorschrift

2-(3,5-Difluorophenyl)-6-hydroxychroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 1.0 g of 2′,5′-dihydroxyacetophenone and 1.12 g of 3,5-difluorobenzaldehyde. The product was recrystallised from acetic acid. 1H NMR (400 MHz, d6-DMSO) δ: 9.47 (s, 1H), 7.30-7.23 (m, 3H), 7.12 (d, 1H, J 2.9 Hz), 7.06 (dd, 1H, J 8.8, 2.9 Hz), 7.00 (d, 1H, J 8.8 Hz), 5.60 (dd, 1H, J 13.1, 2.8 Hz), 3.15 (dd, 1H, J −16.8, 13.1 Hz), 2.85 (dd, 1H, J −16.8, 2.8 Hz).