반응 #75636

반응 방정식

water

3-pentanone

butyllithium

3-allyl-2-fluoro-4-iodopyridine

→

expected product

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

용매

THF

THF

hexane

반응 조건

후처리

1. 1
   기타prepared
2. 2
   workup.STIRRINGThe reaction mixture is stirred for 6 hours at −75° C
3. 3
   기타After returning to room temperature
4. 4
   추출extracted with ethyl acetate
5. 5
   기타The organic phase is dried
6. 6
   농축concentrated
7. 7
   기타purified by chromatography over silica (eluant: cyclohexane/ethyl acetate 8/2)

실험 절차

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.

출처