Water → 3-(3-Allyl-2-fluoro-4-pyridinyl)-3-pentanol

HRID 1635073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635073
C([Li])CCC.[CH2:6]([C:9]1[C:10]([F:16])=[N:11][CH:12]=[CH:13][C:14]=1I)[CH:7]=[CH2:8].[CH3:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21].O>CCCCCC.C1COCC1>[CH2:6]([C:9]1[C:10]([F:16])=[N:11][CH:12]=[CH:13][C:14]=1[C:19]([OH:22])([CH2:20][CH3:21])[CH2:18][CH3:17])[CH:7]=[CH2:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7288Ethyl ketoneHCID 227450382-Fluoro-4-iodo-3-(prop-2-en-1-yl)pyridineHCID 178418339Butyllithium

Produkt 1

HCID 227450133-(3-Allyl-2-fluoro-4-pyridinyl)-3-pentanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

27 ml (43.3 mmol) of 1.6M butyllithium in hexane are added, at −75° C., to a solution of 11.4 g (43.3 mmol) of 3-allyl-2-fluoro-4-iodopyridine (prepared according to the process described in J.O.C., 1993, 58, pp.7832) in 250 ml of THF. After 30 minutes' stirring at −75° C. a solution of 4.6 ml of 3-pentanone in 100 ml of THF is added dropwise. The reaction mixture is stirred for 6 hours at −75° C. After returning to room temperature, the mixture is hydrolysed with 100 ml of water and extracted with ethyl acetate. The organic phase is dried, concentrated and purified by chromatography over silica (eluant:cyclohexane/ethyl acetate 8/2) to yield the expected product.

Aufarbeitung

  1. customprepared
  2. additionis added dropwise
  3. customAfter returning to room temperature
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. concentrationconcentrated
  7. custompurified by chromatography over silica (eluant:cyclohexane/ethyl acetate 8/2)

Quellen und Nachweise

ORD-Eintrag
ord-f1bc394fdec64440979fd9414b8cd82e
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509345B2

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