Реакция #75636

Уравнение реакции

water

3-pentanone

butyllithium

3-allyl-2-fluoro-4-iodopyridine

→

expected product

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

Растворители

THF

THF

hexane

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   workup.STIRRINGThe reaction mixture is stirred for 6 hours at −75° C
3. 3
   ДругоеAfter returning to room temperature
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   ДругоеThe organic phase is dried
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеpurified by chromatography over silica (eluant: cyclohexane/ethyl acetate 8/2)

Методика

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.

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