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

HRID 31188Notes

Reaction equation

HRID 31188 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[F:19][C:20]1[CH:21]=[C:22]([CH:27]2[CH2:36][C:35](=[O:37])[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)[CH:23]=[C:24]([F:26])[CH:25]=1>>[F:19][C:20]1[CH:21]=[C:22]([CH:27]2[CH2:36][CH:35]([OH:37])[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)[CH:23]=[C:24]([F:26])[CH:25]=1

Participants

3

Reactant 2

HCID 179784642-(3,5-Difluorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785182-(3,5-Difluorophenyl)chroman-4,6-diol

Procedure

2-(3,5-Difluorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 800 mg of 2-(3,5-difluorophenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.87 (s, 1H), 7.21-7.17 (m, 3H), 6.88 (d, 1H, J 2.4 Hz), 6.64 (d, 1H, J 8.7 Hz), 6.55 (dd, 1H, J 2.4, 8.7 Hz), 5.47 (d, 1H, J 7.0 Hz), 5.17 (d, 1H, J 10.5 Hz), 4.86 (m, 1H), 2.32 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-6242362e37fb4914a72e47faaa6c43f5
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…