2-Phenylchroman-7-ol → 5-Nitro-2-(2-phenylchroman-7-yloxy)pyridine

HRID 31178Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7](OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=[N:8][CH:9]=1)([O-:3])=[O:2].[C:27]1([CH:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][C:37]([OH:43])=[CH:38][CH:39]=3)[O:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:43][C:37]2[CH:36]=[C:35]3[C:40]([CH2:41][CH2:42][CH:33]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[O:34]3)=[CH:39][CH:38]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 35126382-Phenylchroman-7-ol

HCID 17978512Orm-10103

Product 1

HCID 179785645-Nitro-2-(2-phenylchroman-7-yloxy)pyridine

Procedure

5-Nitro-2-(2-phenylchroman-7-yloxy)pyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 115 mg of 2-phenylchroman-7-ol. The product was purified on preparative TLC-plate covered with silica gel using toluene-ethyl acetate (15:1) as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.8 Hz), 8.60 (dd, 1H, J 9.1, 2.8 Hz), 7.46-7.32 (m, 5H), 7.22 (d, 1H, J 9.1 Hz), 7.20 (d, 1H, J 8.9 Hz), 6.72 (dd, 1H, J 8.9, 2.3 Hz), 6.72 (d, 1H, J 2.3 Hz), 5.16 (dd, 1H, J 10.1, 2.1 Hz), 2.97 (ddd, 1H, J −16.7, 11.3, 5.9 Hz), 2.77 (ddd, 1H, J −16.7, 8.1, 4.5 Hz), 2.20 (m, 1H), 2.02 (m, 1H).

Workup

customThe product was purified on preparative

Sources & evidence

ORD record: ord-c5c8bf839fd2437b8be6919dd571ed22
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

Loading…