Aluminum(III) Chloride → HCID 9859194, compound

HRID 569144Notes

Reaction equation

HRID 569144 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:11]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25](OCC)=[O:26])=[CH:19][CH:18]=2)[CH:15]=[CH:14][N:13]=[CH:12]1>C(OCC)C.O1CCCC1>[N:11]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[CH2:25][OH:26])=[CH:19][CH:18]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 10198998HCID 10198998, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9859194HCID 9859194, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 36 ml of anhydrous diethyl ether was dissolved 1.6 g of anhydrous aluminum chloride, and to the resulting solution was added 1.3 g of lithium aluminum hydride in small portions with ice-cooling over 10 minutes. The resulting mixture was stirred at room temperature for 30 minutes, and to the solution thus obtained was added dropwise a solution of 5.9 g of ethyl (E)-3-[4-(imidazol-1-ylmethyl)phenyl]acrylate in 48 ml of anhydrous tetrahydrofuran with ice-cooling over 30 minutes, after which the resulting mixture was subjected to reaction at room temperature for one hour. Subsequently, 50 ml of hydrous tetrahydrofuran (water content: 10% by volume) was added thereto with ice-cooling, and insolubles were removed by filtration and then washed with five 20-ml portions of methanol. The washings were combined with the filtrate, and the solvent was removed by distillation under reduced pressure. To the resulting oily product were added 100 ml of chloroform and 50 ml of water to form a solution. The organic layer was separated, washed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution, and thereafter dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform:ethanol (20:1 by volume)] to obtain 4.0 g (yield 81.3%) of colorless, oily (E)-3-[4-(imidazol-1-ylmethyl)phenyl]allyl alcohol. This was crystallized from a mixed solvent of methylene chloride and diisopropyl ether to obtain colorless needle crystals having a melting point of 97°-99° C.

Workup

  1. temperaturecooling over 10 minutes
  2. customto the solution thus obtained
  3. temperaturecooling over 30 minutes
  4. customafter which the resulting mixture was subjected to reaction at room temperature for one hour
  5. temperaturewith ice-cooling
  6. custominsolubles were removed by filtration
  7. washwashed with five 20-ml portions of methanol
  8. customthe solvent was removed by distillation under reduced pressure
  9. additionTo the resulting oily product were added 100 ml of chloroform and 50 ml of water
  10. customto form a solution
  11. customThe organic layer was separated
  12. washwashed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe solvent was removed by distillation under reduced pressure
  15. customthe residue thus obtained
  16. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform:ethanol (20:1 by volume)]

Sources & evidence

ORD record
ord-01b5c19b8c974cea90f90356ab38c4c5
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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