Sodium hydride → HCID 14148373, compound

HRID 247608Notes

Reaction equation

HRID 247608 reaction equation
CC(C)([O-])C.[Na+].[H-].[Na+].[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:14]=1[OH:23])([CH3:12])([CH3:11])[CH3:10].[CH2:24]([N:28]1[C:32](=[O:33])[CH:31]=[CH:30][C:29]1=[O:34])[CH2:25][CH2:26][CH3:27]>C(O)(C)(C)C.O.C(O)(=O)C>[C:19]([C:15]1[CH:16]=[C:17]([CH:31]2[CH2:30][C:29](=[O:34])[N:28]([CH2:24][CH2:25][CH2:26][CH3:27])[C:32]2=[O:33])[CH:18]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:14]=1[OH:23])([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 314052,6-Di-tert-butylphenolHCID 2397801-Butyl-1H-pyrrole-2,5-dioneHCID 23676156Sodium t-butoxide

Product 1

HCID 14148373HCID 14148373, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent3×

Procedure

To a solution of sodium tert-butoxide prepared from 2.40 g (0.1 mol) of sodium hydride and 135 ml of tert-butyl alcohol is added dropwise a solution of 20.63 g (0.1 mol) of 2,6-di-tert-butylphenol in 100 ml of tert-butyl alcohol. The reaction mixture is stirred at room temperature for 150 minutes and then to the resultant green solution is added dropwise over 120 minutes a solution of 15.31 g (0.1 mol.) of N-n-butylmaleimide in 50 ml of tert-butyl alcohol. The reaction mixture is stirred at room temperature overnight and is then mixed with 10 ml of glacial acetic acid. The reaction mixture is poured into 1.5 1 of water and the resultant mixture is extracted twice with chloroform. The organic extracts are combined and dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the residue is purified by flash chromatography (3:1 heptane:toluene eluent) to give 4.25 g (12%) of a white solid: mp 109°-112° C.;

Workup

  1. stirringThe reaction mixture is stirred at room temperature overnight
  2. extractionthe resultant mixture is extracted twice with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent is removed in vacuo
  5. customthe residue is purified by flash chromatography (3:1 heptane:toluene eluent)

Sources & evidence

ORD record
ord-0ba0710192d5404fb69e4eb32706a858
Source dataset
uspto-grants-1987_11
Patent number
US04709050

Reaction notes

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