Sodium Hydroxide → 1-(5-Fluoro-1-naphthalenyl)ethanone

Participants

Reaction Steps

Methyl lithium (1.4M solution in ether; 6.6 ml) was added dropwise to a stirred solution of 5-fluoro-1-naphthalene carboxylic acid (870 mg) in dry THF (15 ml) at -78° under nitrogen. The reaction mixture was allowed to warm to room temperature over 2 h and was treated with 2N sodium hydroxide (60 ml). The mixture was extracted with ether (2×30 ml), and the combined, dried organic extracts were evaporated to give the title compound (865 mg) as an oil, t.l.c. (System B, 1:6) Rf 0.3.

Provenance & Evidence