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

HRID 1624335ノート

反応式

HRID 1624335 の反応式
[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]

参加物

5

反応物 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 178418339Butyllithium

生成物 1

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

反応条件

温度
0 °C

実験手順

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 (CH2Cl2/MeOH, 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).

後処理

  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 (CH2Cl2/MeOH, 32:1)

出典と根拠

ORDレコード
ord-e6228182102048b99b4a18dbae22eb06
出典データセット
uspto-grants-2014_07
特許番号
US08778967B2

反応ノート

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