Diisopropylamine → 1-(2-Chlorophenyl)-3-(4-pyridyl)-butane

HRID 257457

반응식

HRID 257457 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH3:14].[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[CH2:24][CH2:25]Br>O1CCCC1.O>[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[CH2:24][CH2:25][CH:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH3:14]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 108224-EthylpyridineHCID 27569631-(2-Bromoethyl)-2-chlorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 197833221-(2-Chlorophenyl)-3-(4-pyridyl)-butane수율 58.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-50 °C

실험 절차

In a 200-ml flask, 0.94g (9.35 mmol) of diisopropyl amine and 15 ml of tetrahydrofuran were placed and cooled to -50° C. Then 6.5 ml (10.3 mmol) of n-butyl lithium (15% n-hexane solution) was added thereto under nitrogen atmosphere. The resulting mixture was stirred for 10 minutes, and a solution of 1.0 g (9.35 mmol) of 4-ethylpyridine dissolved in tetrahydrofuran was added dropwise. After stirring for 30 minutes at -50° C., the reaction temperature was gradually raised up to -10° C., which was kept for 30 minutes, and lowered again to -50° C. A solution of 2.05 g (9.35 mmol) of 2-chlorophenethyl bromide dissolved in tetrahydrofuran was added dropwise to the reaction mixture, and after stirring for 30 minutes at -50° C., the temperature was raised up to room temperature. Subsequently, water was added, tetrahydrofuran was distilled away under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, then dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, to obtain an oil. Said oil was purified by silica gel column chromatography, to obtain 1.35 g of the desired compound (yield: 58.2%).

후처리

  1. additionwas added dropwise
  2. stirringAfter stirring for 30 minutes at -50° C.
  3. temperaturethe reaction temperature was gradually raised up to -10° C., which
  4. waitwas kept for 30 minutes
  5. customlowered again to -50° C
  6. additionwas added dropwise to the reaction mixture
  7. stirringafter stirring for 30 minutes at -50° C.
  8. temperaturethe temperature was raised up to room temperature
  9. distillationtetrahydrofuran was distilled away under reduced pressure
  10. extractionthe residue was extracted with ethyl acetate
  11. washThe extract was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThen, the solvent was distilled away under reduced pressure
  14. customto obtain an oil
  15. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-780b878e9d6541c5b0b544cd0cfb5815
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262420

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