6-Hydroxyflavanone → 6-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one

HRID 31170Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH:27]C1C=C2C(=CC=1)OC(C1C=CC=CC=1)CC2=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15][C:14]3=[O:27])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 27345806-Hydroxyflavanone

HCID 17978512Orm-10103

Product 1

HCID 179785156-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one

Procedure

6-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4one was prepared as described for 5-Nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) using 200 mg of 6-hydroxyflavanone. 1H NMR (400 MHz, d6-DMSO) δ: 9.03 (bs, 1H), 8.64 (d, 1H, J 9.0 Hz), 7.59-7.41 (m, 7H), 7.31 (d, 1H, J 9.0 Hz), 7.23 (d, 1H, 8.8 Hz), 5.75 (dd, 1H, J 12.3, 2.9 Hz), 3.30 (dd, 1H, −16.3, 12.3 Hz), 2.87 (dd, 1H, −16.3, 2.9 Hz).

Sources & evidence

ORD record: ord-26a1bb1afccb4783ab0b0de638e5a4d7
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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