Lithium Chloride → HCID 18916375, compound

HRID 1290615Notes

Reaction equation

HRID 1290615 reaction equation
[Li+].[Cl-:2].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2([CH3:16])[O:15][CH:10]2[C:11]([O:13][CH3:14])=[O:12])[CH:4]=1>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:2][C:9]([C:5]1[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=1)([CH3:16])[CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 18916373HCID 18916373, compound

Product 1

HCID 18916375HCID 18916375, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

0.8 g (20 mmol) of LiCl is dissolved in 100 ml of absolute tetrahydrofuran (THF), the solution is cooled to -20° C., and 20 ml of titanium tetrachloride (1M in dichloromethane) are added dropwise. After the mixture has been stirred for 30 minutes at -20° C., it is cooled to -78° C., and 3.8 g (20 mmol) of methyl 3-(3-pyridyl)-2,3-epoxybutyrate in 50 ml of THF are added dropwise. After the mixture has warmed to room temperature, stirring is continued for 6 hours, the solvent is distilled off, and the residue partitioned between ethyl acetate and water.

Workup

  1. temperatureit is cooled to -78° C.
  2. temperatureAfter the mixture has warmed to room temperature
  3. stirringstirring
  4. waitis continued for 6 hours
  5. distillationthe solvent is distilled off
  6. customthe residue partitioned between ethyl acetate and water

Sources & evidence

ORD record
ord-52b98438c23540af8c5d32212489d667
Source dataset
uspto-grants-1998_05
Patent number
US05753594

Reaction notes

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