Sodium Hydroxide → 3-(4-Chlorophenyl)-3-(3-pyridyl)-2-propen-1-ol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)(O)[CH:9]=[CH2:10])=[CH:4][CH:3]=1.[OH-:18].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH2:10][OH:18])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-ol (0.33 g) was stirred in 25 ml 2 M sulfuric acid overnight at 50° C. The reaction mixture was made alkaline with 45% sodium hydroxide and extracted with ether. The ethereal layer was dried (MgSO4) and evaporated to give 0.30 g of the title compound as an oil. 1H NMR (CDCl3) revealed an approximate Z/E ratio of 60/40:δ3.8 (Br, OH), 4.20 and 4.25 (two doublets, allyl), 6.37 and 6.30 (two triplets, vinyl), 6.9-7.6 (aromatic) and 8.3-8.6 (multiplet, 2,6-pyridyl). This crude product was used directly in the oxidation step according to Example K.