Water → HCID 22119053, compound

HRID 1419112Notes

Reaction equation

HRID 1419112 reaction equation
C(O[C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]([CH3:17])[C:10]=1[CH3:18])=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:6][NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]([CH3:17])[C:10]=1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22048539HCID 22048539, compound

Product 1

HCID 22119053HCID 22119053, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 15 g of N-t-butoxycarbonyl-4-hydroxy-2,3,5-trimethylaniline (prepared as described in Preparation 13) in 200 ml of dehydrated tetrahydrofuran was added to a suspension of 6.8 g of lithium aluminum hydride in 300 ml of dehydrated tetrahydrofuran, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 3 hours, after which it was heated under reflux for 2 hours. At the end of this time, a mixture of 10 ml of water and 30 ml of tetrahydrofuran was added to the reaction mixture in order to destroy any excess of lithium aluminum hydride. The reaction mixture was then stirred at room temperature for 1.5 hours, after which insoluble materials were filtered off with the aid of a Celite (trade mark) filter aid. These materials were washed with ethyl acetate, and the ethyl acetate washings were combined and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:3 by volume mixture of ethyl acetate and hexane as the eluent, to give 5.1 g of the title compound, melting at 120°-122° C.

Workup

  1. temperaturecooling
  2. temperatureafter which it was heated
  3. temperatureunder reflux for 2 hours
  4. additionwas added to the reaction mixture in order
  5. customto destroy any excess of lithium aluminum hydride
  6. stirringThe reaction mixture was then stirred at room temperature for 1.5 hours
  7. filtrationafter which insoluble materials were filtered off with the aid of a Celite (trade mark)
  8. filtrationfilter aid
  9. washThese materials were washed with ethyl acetate
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customthe resulting residue was purified by column chromatography through silica gel using a 1:3
  13. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-69add6c8ab2e4e59933794630d714b89
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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