Allyl Alcohol → HCID 18617566, compound

HRID 1264312Notes

Reaction equation

HRID 1264312 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)=[CH:4][NH:3]1.[CH2:19](O)C=C>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH:16]=[CH2:19])=[O:13])=[CH:10][CH:9]=2)=[CH:4][NH:3]1

Participants

4

Reactant 2

HCID 7858Allyl AlcoholHCID 18617564Ethyl 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoate

Product 1

HCID 18617566HCID 18617566, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst2×

Procedure

To a solution of ethyl 4-(2-oxo-2H-pyridin-5-yl)benzoate (1.24 g, 5.10 mmoles, reference example 36f) in allyl alcohol (50 mL) was added titanium (IV) isopropoxide. The resulting mixture was heated to 70° C. for seven hours at which point more titanium (IV) isopropoxide (3 mL) was added. After 18 hours the heat was removed and 1N HCl solution (50 mL) was added followed by extraction with CH2Cl2 (200 mL). The organic layer was isolated and concentrated to give the title compound in quantitative yield. MS (ion spray) m/z 256 (M+H)+.

Workup

  1. additionwas added
  2. customAfter 18 hours the heat was removed
  3. addition1N HCl solution (50 mL) was added
  4. extractionfollowed by extraction with CH2Cl2 (200 mL)
  5. customThe organic layer was isolated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-62f61683d4c54a9d8b9daa72a035e847
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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