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

HRID 1649542Notes

Reaction equation

HRID 1649542 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 127170981-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-ol

Product 1

HCID 537919533-(4-Chlorophenyl)-3-(3-pyridyl)-2-propen-1-ol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ethereal layer was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-00c615ba059845ce8a3bdc041575bab9
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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