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 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 hr. The reaction was stirred for an additional 2 hr., 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 suspension of 20 gm
- temperaturecooled in ice
- additionwas added 225 ml
- washThe aqueous layer was washed with 2×100 ml
- extractionextracted with ether
- customto give 5.0 gm
Sources & evidence
- ORD record
- ord-38b13558b83045acaf9e380a024e213e
- Source dataset
- uspto-grants-1986_02
- Patent number
- US04568679
Reaction notes
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