Sodium hydride → 2-cyano-3-hydroxy-N-(4-trifluoromethylphenyl)-hexa-2,5-dienamide

反応式

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]([NH:7][C:8](=[O:12])[CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[H-].[Na+].[C:19](Cl)(=[O:23])[CH2:20][CH:21]=[CH2:22]>O1CCCC1>[C:10]([C:9](=[C:19]([OH:23])[CH2:20][CH:21]=[CH2:22])[C:8]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:15])([F:16])[F:1])=[CH:14][CH:13]=1)=[O:12])#[N:11]

参加物

実験手順

6.0 g (0.026 mole) of 4'-trifluoromethyl-cyanoacetanilide in 200 ml of dry tetrahydrofuran were stirred under nitrogen at room temperature and were treated with 1.95 g (0.065 mole) of sodium hydride 80% oil dispersion. The mixture was stirred for a further 30 minutes at room temperature and cooled to -50° C. before the dropwise addition of 3.3 g (0.033 mole) of 3-butenoyl chloride prepared as described in J. Chem. Soc. (1948), p. 661. The mixture was stirred at -50° C. for 2 hours, then was poured onto dilute hydrochloric acid/ice and filtered. The solid was chromatographed over silica gel eluting with dichloromethane to give 2.4 g (31%) of the title compound as colorless crystals and 3 g of starting material were recovered.