Water → HCID 13423334, compound

HRID 1284475Notes

Reaction equation

HRID 1284475 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[C:12]1(/[C:18](/[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C[O-].[Na+]>[CH3:1][O:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]/[CH:19]=[C:18](\[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)/[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13417327HCID 13417327, compound

Product 1

HCID 13423334HCID 13423334, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

p-Toluenesulfonate of (E)-7-phenyl-7-(3-pyridyl)-6-hepten-1-ol (0.2 g, 0.5 mmole) was dissolved in a methanolic solution (1 ml) of 28% sodium methoxide and the solution was allowed to stand at room temperature for 3 days. To the reaction mixture was added water (10 ml) and the product was extracted twice with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography using isopropyl ether-ethyl acetate (1:1) as the developing solvent to give (E)-1-methoxy-7-phenyl-7-(3-pyridyl)-6-heptene (0.1 g, 75%) (Compound I-37) as an oil.

Workup

  1. extractionthe product was extracted twice with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8bb5872352342b289b47a22f358a717
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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