6-Fluoronicotinic Acid → 1-(6-Fluoropyridin-3-yl)ethan-1-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.[CH3:11][Li]>CCOCC>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1)(=[O:10])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 20 gm. (142 mmoles) of 2-fluoro-5-pyridinecarboxylic acid (J. Am. Chem. Soc., 71, 1125 (1949)) in 750 ml of ether, stirred and cooled in ice, was added 225 ml of 1.6M methyl lithium (360 mmoles) in ether over 1 hour. The reaction was stirred for an additional 2 hours, then 300 ml of ice water was added. The aqueous layer was washed with 2×100 ml fresh ether, acidified and extracted with ether to give 5.0 gm. (25%) of unreacted starting acid.
Workup
- additionTo a suspension of 20 gm
- temperaturecooled in ice
- washThe aqueous layer was washed with 2×100 ml fresh ether
- extractionextracted with ether
- customto give 5.0 gm
Sources & evidence
- ORD record
- ord-1d4455da1c9546e8b89847ebc1f02ff6
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04816457
Reaction notes
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