Water → HCID 20109584, compound

HRID 2406567Notes

Reaction equation

HRID 2406567 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[N:15]O)[CH2:13][CH3:14])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([NH2:15])[CH2:13][CH3:14])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 74315225HCID 74315225, compound

Product 1

HCID 20109584HCID 20109584, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(4-(2-methoxyethoxy)phenyl)propan-1-one oxime (1.5 g, 6.7 mmol) in tetrahydrofuran (20 mL) was added dropwise to a stirred suspension of lithium aluminum hydride (0.78 g, 20.55 mmol) in tetrahydrofuran (48 mL) at room temperature under nitrogen. After 18 hours the mixture was heated at reflux for 3 hours, then allowed to cool. 0.8 mL of water was added drop-wise, followed by 0.8 mL of 15% aq sodium hydroxide, and then 2.4 mL of water. After several minutes the mixture was filtered, and the residue washed twice with tetrahydrofuran. The combined filtrate and washings were concentrated in vacuo, leaving 1.34 g of clear golden oil, which was flash chromatographed on a column (5×10 cm) of silica gel eluting with Hxa/EtOAc/acetone 8:1:1 to afford 0.83 g of the product as a clear golden oil; mass spec ES+m/z=210 (m+1).

Workup

  1. temperatureAfter 18 hours the mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. filtrationAfter several minutes the mixture was filtered
  5. washthe residue washed twice with tetrahydrofuran
  6. concentrationThe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-72f39e0b3f6f46f8a71bbd5d8add7c30
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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