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

HRID 47358Notes

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
stirringThe reaction mixture is stirred for 6 hours at −75° C
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-76382879dc454d6b9324a56b45a98434
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699876B2

Reaction notes

Loading…