Diisobutylaluminumhydride → (1,3,5-Triethyl-1H-pyrazol-4-yl)-acetaldehyde

HRID 220461Notes

Reaction equation

HRID 220461 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH2:15][CH3:16])=[N:8][N:9]([CH2:13][CH3:14])[C:10]=1[CH2:11][CH3:12])C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:13]([N:9]1[C:10]([CH2:11][CH3:12])=[C:6]([CH2:5][CH:4]=[O:3])[C:7]([CH2:15][CH3:16])=[N:8]1)[CH3:14]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68595392(1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester

Product 1

HCID 86641649(1,3,5-Triethyl-1H-pyrazol-4-yl)-acetaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of (1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (0.92 g, 3.86 mmol) in tetrahydrofuran (50 mL) to −78° C. and add diisobutylaluminum hydride (16.2 mL, 16.2 mmol, 1 M in toluene) dropwise. Stir the resulting mixture for 5 hr. at −78° C. Quench the reaction mixture with saturated aqueous potassium sodium tartrate solution (30 mL) and ethyl acetate (100 mL) and stir at room temperature for 16 hr. Separate the organic layer; dry (sodium sulfate), filter and concentrate to give the title preparation as an oil (0.65 g, 87%). 1H-NMR (400 MHz, CDCl3) δ 9.57 (t, 1H), 4.01 (q, 2H), 3.38 (d, 2H), 2.57 (q, 4H), 1.39 (t, 3H), 1.20 (t, 3H), 1.15 (t, 3H).

Workup

  1. customat −78° C
  2. customQuench the reaction mixture with saturated aqueous potassium sodium tartrate solution (30 mL) and ethyl acetate (100 mL)
  3. stirringstir at room temperature for 16 hr
  4. customSeparate the organic layer
  5. dry with materialdry (sodium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give the title

Sources & evidence

ORD record
ord-0865bb29ad9f4a6ca24519f5e804bb4e
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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