Imidazole → 1-(2-Methoxyethyl)-1H-imidazole-2-carbaldehyde

HRID 899688Notes

Reaction equation

HRID 899688 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.CN([CH:14]=[O:15])C.C1[CH2:20][O:19][CH2:18][CH2:17]1>>[CH3:20][O:19][CH2:18][CH2:17][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:14]=[O:15]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 164950651-(2-Methoxyethyl)-1H-imidazole-2-carbaldehyde

Conditions

Temperature
0 °C

Procedure

A solution of the imidazole (342 mg, 2.71 mmol) in THF (3.5 mL) was cooled to −78° C. under nitrogen and n-BuLi (2.5M in hexanes, 1.4 mL, 3.5 mmol) was added. The resulting bright yellow solution was stirred at 0° C. for 10 minutes, then DMF (0.5 mL, 6.5 mmol) was added. The reaction was stirred at room temperature for 45 minutes, then was quenched by the addition of saturated aqueous NH4Cl (5 mL). The layers were separated and the aqueous solution was extracted with CH2Cl2 (10 mL×2). The organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2MeOH, 32:1) gave the aldehyde as a yellow liquid (1:1 with DMF, 254 mg, 1.12 mmol, 41%). 1H NMR (CDCl3) δ 3.30 (s, 3H), 3.66 (t, 2H, J=5.1 Hz), 4.58 (t, 2H, J=5.0 Hz), 7.26 (s, 1H), 7.27 (s, 1H), 9.80 (s, 1H).

Workup

  1. stirringThe reaction was stirred at room temperature for 45 minutes
  2. customwas quenched by the addition of saturated aqueous NH4Cl (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous solution was extracted with CH2Cl2 (10 mL×2)
  5. dry with materialThe organic solution was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography on silica (CH2Cl2MeOH, 32:1)

Sources & evidence

ORD record
ord-4fd9cda02acf4360b5cdb34c18661c92
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

Loading…