Ethylene Glycol → 2,6-Diphenyl-4-piperidone Ethylene Ketal

HRID 2254391

반응식

HRID 2254391 반응식
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Si](C)(C)C.[CH2:25](O)[CH2:26][OH:27]>>[CH2:26]1[O:27][C:11]2([CH2:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:8][CH:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10]2)[O:13][CH2:25]1

참가 물질

4

반응물 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 28287082,6-Di(phenyl)-4-piperidone

생성물 1

HCID 218013452,6-Diphenyl-4-piperidone Ethylene Ketal수율 69%

반응 조건

온도
0 °C

실험 절차

To a stirred suspension of 10.0 g (40 mmol) of 2,6-diphenyl-4-piperidone in 150 mL of ethylene glycol chilled to 0° C. is added 35 mL (275 mmol) of chlorotrimethylsilane over a one-hour period. The reaction mixture is warmed to room temperature and stirred for 15 hours. The reaction mixture is then quenched by carefully pouring it into 600 mL of saturated aqueous sodium bicarbonate solution. The product is extracted into ether (4×200 mL). The ether solution is dried over anhydrous sodium sulfate and the solvent is removed under reduced pressure. The residue is recrystallized from methanol to yield 8.1 g (69%) of the title compound as a white solid, melting at 125°-127° C.

후처리

  1. temperatureThe reaction mixture is warmed to room temperature
  2. customThe reaction mixture is then quenched
  3. additionby carefully pouring it into 600 mL of saturated aqueous sodium bicarbonate solution
  4. extractionThe product is extracted into ether (4×200 mL)
  5. dry with materialThe ether solution is dried over anhydrous sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is recrystallized from methanol

출처 및 근거

ORD 기록
ord-8e11a672ee064eafbf677ef95993f135
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05235056

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