Sodium Hydroxide → 3-(4-Chlorophenyl)-3-(3-pyridyl)-2-propen-1-ol

Participants

Reaction Steps

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.

Provenance & Evidence