2-Ethylbutyraldehyde → HCID 68593352, compound

HRID 748067Notes

Reaction equation

HRID 748067 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-22ef515c1a0e407fae3abea73fd0f058
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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