Potassium Carbonate → 3-cyclopropyl-2-methyl-3H-imidazole-4-carbaldehyde

HRID 1350718ノート

反応式

HRID 1350718 の反応式
Cl.[CH:2]1([NH:5][C:6](=[NH:8])[CH3:7])[CH2:4][CH2:3]1.Br[C:10](=[CH:13]OC(C)C)[CH:11]=[O:12].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.O>[CH:2]1([N:5]2[C:10]([CH:11]=[O:12])=[CH:13][N:8]=[C:6]2[CH3:7])[CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178465552HCID 178465552、化合物

生成物 1

HCID 210973073-cyclopropyl-2-methyl-3H-imidazole-4-carbaldehyde収率 35.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

Ethyl acetimidate hydrochloride (5.0 g, 40 mmol) and cyclopropylamine (2.3 mL, 40 mL) were dissolved in 45 mL of EtOH and heated to 85° C. in a sealed pressure vessel overnight. The mixture was cooled and concentrated to provide N-cylcopropyl-acetamidine hydrochloride as a viscous oil. N-Cyclopropyl-acetamidine hydrochloride (1.00 g, 7.43 mmol) and 2-bromo-3-isopropoxy-propenal (Shilcrat, S. C. et al. J. Org. Chem., 1997, 62, 8449–8454) (1.45 g, 7.50 mmol) were dissolved in 13 mL of CHCl3 and 1.6 mL of water. Then K2CO3 (1.5 g, 11 mmol) was added and the mixture was stirred overnight. The reaction was partitioned between CH2Cl2 (60 mL) and water (30 mL). The layers were separated and the aqueous portion was extracted with CH2Cl2 (40 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4), filtered, concentrated, and chromatographed to provide 400 mg of 3-cyclopropyl-2-methyl-3H-imidazole-4-carbaldehyde.

後処理

  1. customThe reaction was partitioned between CH2Cl2 (60 mL) and water (30 mL)
  2. customThe layers were separated
  3. extractionthe aqueous portion was extracted with CH2Cl2 (40 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed

出典と根拠

ORDレコード
ord-ae9262e308344a39b6e62fb134111b12
出典データセット
uspto-grants-2007_05
特許番号
US07214802B2

反応ノート

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