Water → HCID 66822056, compound

HRID 2406557Notes

Reaction equation

HRID 2406557 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:15]O)[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH2:15])[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride3×HCID 86663514HCID 86663514, compound

Product 1

HCID 66822056HCID 66822056, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(4-(methoxymethoxy)phenyl)butan-1-one oxime (3.4 g, 15.2 mmol) in tetrahydrofuran (50 mL) was added drop-wise to a stirred suspension of lithium aluminum hydride (1.83 g, 45.7 mmol) in tetrahydrofuran (100 mL) at room temp under nitrogen. After the initial foaming subsided the mixture was gradually heated to reflux. After 7 hours under reflux the mixture was allowed to cool, and an additional 1.0 g of lithium aluminum hydride was added to the mixture, which was reheated at reflux for 4 hours and then again allowed to cool. An additional 0.2 g of lithium aluminum hydride was added and the mixture was reheated at reflux for 1 hour and then allowed to cool. 3 mL of water was added drop-wise, followed by 3 mL of 15% aq sodium hydroxide, and then 9 mL of water. After stirring until the precipitate was well-granulated, the mixture was filtered and the residue washed twice with tetrahydrofuran. The filtrate/washings were concentrated in vacuo and the residue dissolved in dichloromethane and dried over magnesium sulfate. The solvent was removed in vacuo, leaving 2.9 g of purplish syrupy residue, which was flash chromatographed on a column (50×90 mm) of silica gel, eluting with Hxa/EtOAc/acetone 8:1:1 to afford 0.4 g of pure product as a clear golden oil, plus 1.4 g (57% total) of material of slightly lesser purity.

Workup

  1. temperaturewas gradually heated to reflux
  2. temperatureAfter 7 hours under reflux the mixture
  3. temperatureto cool
  4. temperatureat reflux for 4 hours
  5. temperatureto cool
  6. temperatureat reflux for 1 hour
  7. temperatureto cool
  8. filtrationthe mixture was filtered
  9. washthe residue washed twice with tetrahydrofuran
  10. concentrationThe filtrate/washings were concentrated in vacuo
  11. dissolutionthe residue dissolved in dichloromethane
  12. dry with materialdried over magnesium sulfate
  13. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cb49f44e5aad47799a8f2d6557139256
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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