Diethyl Carbonate → 3-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester

HRID 12462ノート

反応式

HRID 12462 の反応式
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[CH3:2].[Li]CCCC.CCCCCC.[C:29](=O)([O:33]CC)[O:30][CH2:31][CH3:32]>C1COCC1.O>[CH2:31]([O:30][C:29]([C:7]1[N:3]([CH2:1][CH3:2])[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)=[N:5][CH:6]=1)=[O:33])[CH3:32]

参加物

7

反応物 4

HCID 7766Diethyl CarbonateHCID 8058HexaneHCID 572422981-ethyl-2-naphthalen-1-yl-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 686289133-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 1-ethyl-2-naphthalen-1-yl-1H-imidazole (1.11 g, 5 mmol) in anhydrous THF (30 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 3.44 ml, 5.5 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, followed by the addition of diethyl carbonate (1.77 g, 15 mmol, 3.0 eq.). The resulting solution is stirred at −78° C. for 30 min, warmed to rt slowly, and stirred for an additional 30 min at rt. Water (30 ml) is added to quench the reaction, and THF is evaporated under reduced pressure. The residue is extracted with EtOAc (30 ml×2) and the combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1) to give 3-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester. LCMS 295 (M+1).

後処理

  1. stirringThe resulting solution is stirred at −78° C. for 30 min
  2. temperaturewarmed to rt slowly
  3. stirringstirred for an additional 30 min at rt
  4. customto quench
  5. customthe reaction, and THF
  6. customis evaporated under reduced pressure
  7. extractionThe residue is extracted with EtOAc (30 ml×2)
  8. washthe combined organic layers are washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude product is purified through silica gel chromatography (hexanes/EtOAc, from 8:1 to 4:1)

出典と根拠

ORDレコード
ord-2a1bb3c7e7b748988571efc43482488c
出典データセット
uspto-grants-2010_06
特許番号
US07728009B1

反応ノート

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