Dimethylformamide → Ethyl 1-tetradecylpyrrole-3-carboxylate

HRID 129348

反応式

HRID 129348 の反応式
CN(C)C=O.[H-].[Na+].[NH:8]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O>[CH2:32]([N:8]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]1)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8208Myristyl bromideHCID 24758Sodium hydrideHCID 13070719Ethyl 1H-pyrrole-3-carboxylate

生成物 1

HCID 15023354Ethyl 1-tetradecylpyrrole-3-carboxylate収率 94.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To dry dimethylformamide (DMF) (15 ml) was added 0.84 g (21 mmol) of sodium hydride (60% oil dispersion), and then 2.78 g (20 mmol) of ethyl pyrrole-3-carboxylate was added portionwise thereto under ice-cooling. After stirring at room temperature for 10 minutes, 6.65 g (24 mmol) of bromotetradecane was added dropwise under ice-cooling. The mixture was stirred for 3.5 hours at room temperature, and then 30 ml of water was added thereto. The resulting mixture was extracted with 70 ml of ethyl acetate, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After removing the solvent, the remaining oil was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/20-1/10) to obtain 6.33 g (89.0% yield) of ethyl 1-tetradecylpyrrole-3-carboxylate as white crystals, m.p. 32°-33° C.

後処理

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. stirringThe mixture was stirred for 3.5 hours at room temperature
  4. extractionThe resulting mixture was extracted with 70 ml of ethyl acetate
  5. washwashed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing the solvent
  8. customthe remaining oil was purified

出典と根拠

ORDレコード
ord-c0ba77a295b6402a95171267e1c0cb30
出典データセット
uspto-grants-1995_11
特許番号
USRE035096

関連ノート

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