2-(3-Fluorophenyl)chroman-6-ol → 3,4-Dihydro-2H-1-benzopyran-6-ol

HRID 31327Notes

Reaction equation

HRID 31327 reaction equation
FC1C=C([CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=3)[O:9]2)C=CC=1.[N+](C1C=C(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=1)([O-])=O>>[O:9]1[C:10]2[C:15](=[CH:14][C:13]([OH:18])=[CH:12][CH:11]=2)[CH2:16][CH2:17][CH2:8]1

Participants

3

Reactant 2

HCID 179784712-(3-Fluorophenyl)chroman-6-olHCID 179785222-(3-Nitrophenyl)chroman-4,6-diol

Product 1

HCID 151223383,4-Dihydro-2H-1-benzopyran-6-ol

Procedure

2-3-Nitrophenyl)chroman-6-ol was prepared as described for 2-(3-fluorophenyl)chroman-6-ol in Example 9(c) starting from 2-(3-nitrophenyl)chroman-4,6-diol. 1H NMR (300 MHz, d6-DMSO) δ: 8.80 (s, 1H), 8.26 (s, 1H), 8.19 (dd, 1H, J 8.1, 2.3 Hz), 7.90 (d, 1H, J 7.9Hz), 7.70 (t, 1H, J 15.9, 7.9 Hz), 6.70 (d, 1H, J 8.4 Hz), 6.51-6.55 (m, 2H), 5.19 (dd, 1H, J 10.0, 2.0), 2.86-2.91 (m, 1H), 2.61-2.68 (m, 1H), 2.17-2.23 (m, 1H), 1.91-1.97 (m, 1H).

Sources & evidence

ORD record
ord-467284f103f0435696cb7ce15456762f
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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