Water → HCID 70454989, compound

HRID 1284476Notes

Reaction equation

HRID 1284476 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8](\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H-].[Na+].O>O1CCCC1.CN(C)C=O>[O:27]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8](\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 70406248HCID 70406248, compound

Product 1

HCID 70454989HCID 70454989, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(E)-1-Iodo-7-phenyl-7-(3-pyridyl)-6-heptene (0.6 g, 1.6 mmoles) and phenol (0.2 g, 2.1 mmoles) were dissolved in a mixture of tetrahydrofuran (10 ml) and dimethylformamide (2 ml), and sodium hydride (60% dispersion in oil, 0.1 g, 2.5 mmoles) was added to the solution. The mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added water (20 ml), followed by extraction of the product with ether. 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 (2.1) as the developing solvent to give (E)-1-phenoxy-7-phenyl-7-(3-pyridyl)-6-heptene (0.5 g, 73%) (Compound Id-38) as an oil.

Workup

  1. additionwas added to the solution
  2. extractionfollowed by extraction of the product with ether
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bacc0aab783243a3ac8e1e2b470a0453
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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