Orm-10103 → 6-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-ol

HRID 31173

Reaktionsgleichung

Reaktionsgleichung von HRID 31173
[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].C1(C2CC(O)C3C(=CC=C(O)C=3)[O:34]2)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[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][CH:14]3[OH:34])=[N:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 17978512Orm-10103HCID 179786312-Phenylchroman-4,6-diol

Produkt 1

HCID 179785596-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584019Toluene ethylacetateLösungsmittel

Versuchsvorschrift

6-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1 (b) starting from 1.5 g of 2-phenylchroman-4,6-diol. The product was passed through a silica gel column using toluene-ethyl acetate (4:1) as an eluant and then crystallised from 2-propanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.7 Hz), 8.61 (dd, 1H, J 9.1, 2.7 Hz), 7.50-7.36 (m, 5H), 7.25 (d, 1H, J 2.7 Hz), 7.22 (d, 1H, 9.1 Hz), 7.00 (dd, 1H, J 8.7, 2.7 Hz), 6.88 (d, 1H, J 8.7 Hz), 5.65 (d, 1H, J 6.3 Hz), 5.30 (dd, 1H, J 11.9, 1.3 Hz), 4.99 (m, 1H), 2.33 (m, 1H), 1.98 (m, 1H).

Aufarbeitung

  1. customcrystallised from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-dd62942f13f44d41aa37a804c3ddbf1e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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