Diisobutylaluminum hydride → HCID 86677485, compound

HRID 1621132Notes

Reaction equation

HRID 1621132 reaction equation
[CH3:1][C:2]1[C:3]([C:13](OCC)=[O:14])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.CC(C[AlH]CC(C)C)C.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([CH2:13][OH:14])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 516920Potassium bisulfateHCID 21679695HCID 21679695, compound

Product 1

HCID 86677485HCID 86677485, compoundYield 137.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of ethyl 4-methyl-1-phenyl-1H-pyrazole-3-carboxylate (100 mg, 434 μmol) in toluene (1 mL) cooled to −78° C. was added dropwise DIBAL-H (1M solution in toluene, 868 μL, 868 μmol) keeping the temperature below −68° C. The reaction mixture was stirred at −78° C. for 30 min and at −15° C. for 1 h. At that temperature, KHSO4 (10% aqueous solution, 10 mL) was added dropwise and the resulting reaction mixture was extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (1×30 mL) and brine (1×20 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 112 mg crude material. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as yellow viscous oil (52 mg, 276 μmol, 63.6%).

Workup

  1. customthe temperature below −68° C
  2. customthe resulting reaction mixture
  3. extractionwas extracted with ethyl acetate (2×50 mL)
  4. washThe organic phases were washed with water (1×30 mL) and brine (1×20 mL)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-498ba722911d4ebe9345405d97839457
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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