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

HRID 1635073Notes

Reaction equation

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]

Participants

Conditions

Temperature: -75 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-f1bc394fdec64440979fd9414b8cd82e
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509345B2

Reaction notes

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