Diisobutylaluminum hydride → HCID 21097259, compound

HRID 1350786Notes

Reaction equation

HRID 1350786 reaction equation
C[O:2][C:3](=O)[C:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([O:16][CH3:17])=[C:9]([N+:18]([O-:20])=[O:19])[CH:8]=1)([CH3:6])[CH3:5].CC(C[AlH]CC(C)C)C.[O-]S([O-])(=O)=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.C(Cl)Cl.CCOC(C)=O.CO>[CH3:17][O:16][C:10]1[C:9]([N+:18]([O-:20])=[O:19])=[CH:8][C:7]([C:4]([CH3:6])([CH3:5])[CH2:3][OH:2])=[CH:12][C:11]=1[N+:13]([O-:15])=[O:14]

Participants

9

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24436Sodium SulfateHCID 86604275HCID 86604275, compound

Product 1

HCID 21097259HCID 21097259, compoundYield 49.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 1.30 g (4.35 mmol) of 2-(4-methoxy-3,5-dinitro-phenyl)-2-methyl-propionic acid methyl ester in 30 mL of THF was added dropwise 17 mL (17 mmol) of 1.0 M DIBAL in CH2Cl2. After stirring an additional 4 h, 2 mL of MeOH and then saturated Na2SO4 (2 mL) were slowly added. The resulting suspension was rapidly stirred for 20 min then 40 mL of EtOAc was added followed by MgSO4. The resulting mixture was then stirred at rt for an additional 30 min. The mixture was filtered through celite, and the filter cake was washed with EtOAc. The filtrate was concentrated to provide 580 mg of 2-(4-methoxy-3,5-dinitro-phenyl)-2-methyl-propan-1-ol.

Workup

  1. stirringThe resulting suspension was rapidly stirred for 20 min
  2. stirringThe resulting mixture was then stirred at rt for an additional 30 min
  3. filtrationThe mixture was filtered through celite
  4. washthe filter cake was washed with EtOAc
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-59f3f0a8d44e4e7696c04193cd68af6d
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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