6-Fluoronaphthalene-1-carboxylic acid → HCID 14987239, compound
Reaction equation
[CH3:1][Li].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([C:14]([OH:16])=O)=[CH:9][CH:8]=[CH:7]2>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([C:14](=[O:16])[CH3:1])=[CH:9][CH:8]=[CH:7]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl lithium (1.59M solution in ether; 4.2 ml) was added dropwise to a stirred solution of 6-fluoro-1-naphthalene carboxylic acid (640 mg) in dry THF (10 ml) at -78° under nitrogen. The solution was stirred at -78° for 2 h and was slowly allowed to warm to -15°. The solution was quenched with saturated aqueous ammonium chloride (1 ml) and partitioned between 2N sodium hydroxide (25 ml) and ethyl acetate (25 ml). The organic phase was dried and evaporated to give the title compound (404 mg) as an oil, t.l.c. (System B, 1:6) Rf 0.2.