Allyl Alcohol → furo[3,2-b]pyridin-3(2H)-one

HRID 1846232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846232
[CH2:1]([O:4][C:5]1[C:6](Br)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=C.N(C(OCC)=O)=NC(OCC)=[O:15].BrC1C(O)=CC=CN=1.C(O)C=C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.C([O-])(O)=O.[Na+]>[O:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2](=[O:15])[CH2:1]1

Komponenten

8

Edukt 5

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 230702-Bromo-3-pyridinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23028574Pyridine, 2-bromo-3-(2-propenyloxy)-

Produkt 1

HCID 14199079furo[3,2-b]pyridin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-(allyloxy)-2-bromopyridine. Diethyl azodicarboxylate (1 eq.) is added dropwise to a stirring mixture of 2-bromo-3-hydroxypyridine (0.92 eq,), allyl alcohol (0.92 eq), and PPh3 (1.1 eq) in THF (0.2 M) at 0° C. under a N2 atmosphere. The reaction mixture is warmed to 50° C. in an oil bath. Reaction progress is monitored by TLC until judged complete. The reaction mixture is cooled to ambient temperature and diluted with saturated NaHCO3 solution. The aqueous solution is extracted with EtOAc, and the organic layer is dried over Na2SO4 and concentrated. The product that may be thus obtained is purified by column chromatography to afford the title compound.

Aufarbeitung

  1. customReaction progress
  2. temperatureThe reaction mixture is cooled to ambient temperature
  3. extractionThe aqueous solution is extracted with EtOAc
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. customThe product that may be thus obtained
  7. customis purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ab00b8297804d19afbc1f032ca3aa75
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952009B2

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