Hydrochloric Acid → 1,3-Difluoro-5-[3-hydroxy-3-(thiazol-2-yl)propen-3-yl]benzene

反応式

[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:16]([Mg]Br)=[CH2:17].Cl>C1COCC1>[F:8][C:6]1[CH:5]=[C:4]([C:9]([OH:10])([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:16]=[CH2:17])[CH:3]=[C:2]([F:1])[CH:7]=1

参加物

実験手順

To a solution of (3,5-difluorophenyl)(thiazol-2-yl)methanone (1 g, 4.4 mmol, Step 2) in dry THF (40 mL) was added at 0° C. (4.4 mL, 4.4 mmol) of a 1.0M THF solution of vinyl magnesium bromide (Aldrich). The reaction mixture was stirred for 30 min. and then transferred to a 1N aqueous HCl solution. The resulting mixture was extracted with EtOAc and the combined organic phase were washed with brine, dried over MgSO4 and evaporated to give a residue which was chromatographed on silica gel eluting with 85:15 mixture of hexane:EtOAc to afford 635 mg (56%) of the title compound.