2-Ethylbutyraldehyde → HCID 68593352, compound

HRID 2243143Notes

Reaction equation

HRID 2243143 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH2:18]([CH:20]([CH2:23][CH3:24])[CH:21]=[O:22])[CH3:19].[NH4+].[Cl-]>CCOCC>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:21]([OH:22])[CH:20]([CH2:23][CH3:24])[CH2:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 73592-EthylbutyraldehydeHCID 25517Ammonium ChlorideHCID 779181-BenzylimidazoleHCID 178418339Butyllithium

Product 1

HCID 68593352HCID 68593352, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a chilled reaction vessel at −45° C. containing 1-benzyl-1H-imidazole (3.0 g, 19.0 mmol) in Et2O (100 mL) was added a solution of n-butyllithium (2.5M in hexanes, 10.8 mL, 26.9 mmol) dropwise. After 30 min, the reaction vessel was cooled to −78° C. and 2-ethylbutyraldehyde (2.8 mL, 22.8 mmol) was added dropwise. The reaction mixture was warmed to 0° C. and stirred for 15 min, then poured into sat. aqueous NH4Cl and extracted with Et2O. The organic layer was washed with H2O, dried over MgSO4, filtered and concentrated in vacuo. The resulting yellow oil was purified by column chromatography (SiO2, EtOAc/hexane, 3:2, then 7:3) to yield a clear oil in 69% yield.

Workup

  1. customTo a chilled reaction vessel at −45° C.
  2. temperatureThe reaction mixture was warmed to 0° C.
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting yellow oil was purified by column chromatography (SiO2, EtOAc/hexane, 3:2
  9. custom7:3) to yield a clear oil in 69% yield

Sources & evidence

ORD record
ord-a44e7f27a04d4c39a6684a1d3272904f
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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