2-(4-Ethylphenyl)chroman-6-ol → 2-[2-(4-Ethylphenyl)chroman-6-yloxy]-5-nitropyridine

HRID 31202Notes

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].[CH2:27](C1C=CC(C2CCC3C(=CC=C(O)C=3)O2)=CC=1)[CH3:28]>>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([CH:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([O:10][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:12]=3)[O:17]2)=[CH:26][CH:25]=1)[CH3:28]

Participants

Reactant 2

HCID 179784982-(4-Ethylphenyl)chroman-6-ol

HCID 17978512Orm-10103

Product 1

HCID 179786442-[2-(4-Ethylphenyl)chroman-6-yloxy]-5-nitropyridine

Procedure

2-[2-(4-Ethylphenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 205 mg of 2-(4-ethylphenyl)chroman-6-ol. The product was recrystallised from a mixture of 2-propanol and acetone. 1H NMR (400 MHz, CDCl3) δ: 9.04 (d, 1H, J 2.8 Hz), 8.60 (dd, 1H, J 9.1, 2.8 Hz), 7.36 (d, 2H, J 8.1 Hz), 7.24 (d, 2H, J 8.1 Hz), 7.20 (d, 1H, J 9.1 Hz), 7.00 (d, 1H, J 2.7 Hz), 6.96 (dd, 1H, J 8.8, 2.7 Hz), 6.89 (d, 1H, J 2.7 Hz), 5.11 (dd, 1H, J 10.1, 2.2 Hz), 2.98 (m, 1H), 2.75 (m, 1H), 2.62 (q, 2H, J 7.5 Hz), 2.16 (m, 1H), 2.01 (m, 1H), 1.19 (t, 3H, J 7.5 Hz).

Workup

customThe product was recrystallised from a mixture of 2-propanol and acetone

Sources & evidence

ORD record: ord-e9032c357d4f4e9bb1ac4c9e4fbdd896
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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