Water → HCID 15057231, compound

HRID 2073716Notes

Reaction equation

HRID 2073716 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH2:26][CH3:27])[CH2:10][C:11]([NH:13][C:14]1[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:23]([CH3:25])[CH3:24])=O)[CH3:8].O.[OH-].[Na+]>O1CCCC1>[CH2:26]([N:9]([CH2:7][CH3:8])[CH2:10][CH2:11][NH:13][C:14]1[C:19]([CH:20]([CH3:21])[CH3:22])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:23]([CH3:25])[CH3:24])[CH3:27]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15057229HCID 15057229, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15057231HCID 15057231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 mL of tetrahydrofuran under a nitrogen atmosphere add 8.8 g (0.23 mol) of lithium aluminum hydride. Add dropwise a solution of 33.8 g (0.12 mol) of 2-(diethylamino)-N-(2,6-bis(1-methylethyl)phenyl)acetamide in 150 mL of tetrahydrofuran. When the addition is complete allow the reaction to stir at reflux. Monitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2 :MeOH, 9:1). Upon completion of the reaction add 1 mL of water, 1 mL of 15% NaOH and 3 mL of water per gram of lithium aluminum hydride. The solid material is removed by suction filtration through celite and the solvent is removed in vacuo. Recrystallize the solid from hexane to give the title compound.

Workup

  1. additionWhen the addition
  2. customthe reaction
  3. temperatureat reflux
  4. customMonitor the progress of the reaction by thin-layer chromatography on silica gel (CH2Cl2 :MeOH, 9:1)
  5. customThe solid material is removed by suction filtration through celite
  6. customthe solvent is removed in vacuo
  7. customRecrystallize the solid from hexane

Sources & evidence

ORD record
ord-6dce2114824343fc99f5bf3b3685f224
Source dataset
uspto-grants-1990_04
Patent number
US04920116

Reaction notes

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