Sodium Hydroxide → HCID 67436691, compound

Participants

Reaction Conditions

Reaction Steps

Under argon and at 0° C., 4 ml of lithium aluminium hydride solution (1M in diethyl ether, 4.00 mmol) are added to a solution of 1.1 g (4.00 mmol) of methyl 1-(2-chloroethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate in 20 ml of tetrahydrofuran. The mixture is then stirred at 0° C. for 2 h. At 0° C., 5M of aqueous NaOH solution are then carefully added dropwise to the reaction mixture until the evolution of hydrogen has stopped. The suspension formed is decanted off and the solvent is removed. The crude product obtained is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 900 mg (86%) of the desired product; log P(HCOOH): 1.84; 1H-NMR (MeCN-d3): δ=7.81-7.77 (m, 2H), 7.16-7.12 (m, 2H), 6.53 (s, 1H), 4.64 (d, 2H), 4.45 (t, 2H), 4.00 (t, 2H).

Provenance & Evidence