Sodium hydride → HCID 59556324, compound

Participants

Reaction Steps

1.0 g (4-Cyano-3-fluoro-benzyl)-phosphonic acid diethyl ester was dissolved in 50 ml tetrahydrofuran and cooled in an ice bath. At 0° C. 103 mg sodium hydride were added and the mixture stirred for fifteen minutes. Then 1.2 g 1-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-pentan-1-one, dissolved in 20 ml tetrahydrofuran, were added dropwise. The cooling bath was removed and the reaction mixture stirred at room temperature for two hours. Then 1.0 g (4-Cyano-3-fluoro-benzyl)-phosphonic acid diethyl ester and 103 mg sodium hydride were added and the reaction mixture stirred for an additional hour. Then 20 ml water were added and the mixture extracted five times with portions of 25 ml ethyl acetate. The combined organic layers were dried over MgSO4, then the solvent was removed in vacuo to obtain 1.6 g 2-Fluoro-4-{(E)-2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-hex-1-enyl}-benzonitrile as a yellow oil.

Provenance & Evidence