Dimethylformamide → Ethyl 1-tetradecylpyrrole-3-carboxylate

HRID 129348

반응식

HRID 129348 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 15023354Ethyl 1-tetradecylpyrrole-3-carboxylate수율 94.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0ba77a295b6402a95171267e1c0cb30
출처 데이터셋
uspto-grants-1995_11
특허 번호
USRE035096

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