2-Acetylhydroquinone → 6-Hydroxy-2-(2-trifluoromethylphenyl)chroman-4-one

반응식

F[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][C:32]([F:42])([F:41])C1C=CC=CC=1C=O>>[OH:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C:32]([F:42])([F:41])[F:31])[CH2:17][C:16]2=[O:18]

참가 물질

반응물 3

HCID 102792-Acetylhydroquinone

HCID 123067o-(Trifluoromethyl)benzaldehyde

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

생성물 1

HCID 179786236-Hydroxy-2-(2-trifluoromethylphenyl)chroman-4-one

실험 절차

6-Hydroxy-2-(2-trifluoromethylphenyl)chroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 3.0 g of 2′,5′-dihydroxyacetophenone and 3.0 ml of 2-trifluoromethylbenzaldehyde. The product was triturated from ethanol. 1H NMR (300 MHz, d6-DMSO) δ: 9.48 (s, 1H), 8.07 (m, 1H), 7.86-7.79 (m, 2H), 7.66 (m, 1H), 7.15 (d, 1H, J 3.0 Hz), 7.06 (dd, 1H, J 8.8, 3.0 Hz), 6.95 (d, 1H, J 8.8 Hz), 5.70 (dd, 1H, J 13.8, 2.4 Hz), 3.38 (dd, 1H, J −16.9, 13.8 Hz), 2.66 (dd, 1H, J −16.9, 3.0 Hz).