Reaktion #75636

Reaktionsgleichung

water

3-pentanone

butyllithium

3-allyl-2-fluoro-4-iodopyridine

→

expected product

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

Lösungsmittel

THF

THF

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   workup.STIRRINGThe reaction mixture is stirred for 6 hours at −75° C
3. 3
   SonstigeAfter returning to room temperature
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   SonstigeThe organic phase is dried
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by chromatography over silica (eluant: cyclohexane/ethyl acetate 8/2)

Vorschrift

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.

Quelle