Allyl Alcohol → 2-(Allyloxy)-5-chloro-3-nitropyridine

HRID 1373767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373767
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH:12]1[CH:17]=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=C[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C=C>C1COCC1>[CH2:17]([O:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)[CH:12]=[CH2:13]

Komponenten

6

Edukt 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 178526657HCID 178526657, Verbindung

Produkt 1

HCID 210753722-(Allyloxy)-5-chloro-3-nitropyridineAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 5-chloro-3-nitro-pyridin-2-ol (0.600 g, 3.4 mmol), DBAD (1.19 g, 5.16 mmol), triphenylphosphine-polymer supported (3 mmol/g, 1.70 g, 5.16 mmol) in THF (18 mL) was added allyl alcohol (0.42 mL, 6.12 mmol). The reaction mixture was stirred at room temperature overnight, filtered through celite, and concentrated. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (95:5 to 1:1) to give 0.120 g (15%) of the desired product. MS (DCI/NH3) m/z: 214.9 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 5.01 (ddd, J=5.34, 1.40, 1.40 Hz, 2 H) 5.32 (dd, J=10.51, 1.36 Hz, 1 H) 5.49 (dd, J=17.12, 1.53 Hz, 1 H) 6.06 (m, 1 H) 8.28 (d, J=2.37 Hz, 1 H) 8.34 (d, J=2.37 Hz, 1 H).

Aufarbeitung

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with hexane/ethyl acetate (95:5 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0fa675ad2edc4d09a2be2e8ea6a94f23
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163939B2

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