7-Hydroxyflavanone → 2-Phenylchroman-7-ol

HRID 31177Notes

Reaction equation

[N+](C1C=CC(OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=NC=1)([O-])=O.[OH:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32](=O)[CH2:33][CH:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:35]2)=[CH:30][CH:29]=1>>[C:38]1([CH:34]2[CH2:33][CH2:32][C:31]3[C:36](=[CH:37][C:28]([OH:27])=[CH:29][CH:30]=3)[O:35]2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

Reactant 2

HCID 18907-Hydroxyflavanone

HCID 17978512Orm-10103

Product 1

HCID 35126382-Phenylchroman-7-ol

Procedure

2-Phenyl-chroman-7-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(a) starting from 1.0 g of 7-hydroxy-flavanone. The product was purified by column chromatography using heptane-ethyl acetate (2:1) as an eluant. 1H NMR (400 MHz, CD3OD) δ: 7.41-7.28 (m, 5H), 6.86 (d, 1H, J 8.2 Hz), 6.32 (dd, 1H, J 8.2, 2.4 Hz), 6.29 (d, 1H, J 2.4 Hz), 5.00 (dd, 1H, J 9.9, 2.4 Hz), 2.84 (m, 1H), 2.64 (m, 1H), 2.15 (m, 1H), 1.99 (m, 1H).

Workup

customThe product was purified by column chromatography

Sources & evidence

ORD record: ord-003a647121e44733b550aaa6cb9b1b88
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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