Chloro(chloromethyl)[bis(4-fluorophenyl)]silane → [bis(4-Fluorophenyl)](1H-imidazol-1-ylmethyl)silane

HRID 371314노트

반응식

HRID 371314 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(Cl)[CH2:9]Cl)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.[K].[H-].C([Al+]CC(C)C)C(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([SiH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 13392398Chloro(chloromethyl)[bis(4-fluorophenyl)]silaneHCID 21225700DiisobutylaluminumhydrideHCID 67086713Potassium imidazole

생성물 1

HCID 123558487[bis(4-Fluorophenyl)](1H-imidazol-1-ylmethyl)silane

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

To a solution of 3.0 g (9.9 mmol) of bis(4-fluorophenyl)chlorochloromethylsilane and 50 mg of tetrabutylammonium hydrogen sulfate in 10 ml of toluene is added 2.2 g (20.5 mmol) of potassium imidazole. The resulting exotherm is controlled by cooling with ice-water. Th solution is heated at reflux for 5 hours and then was cooled to -70° C. A solution of 10.5 ml (10.5 mmol) of diisobutylaluminum hydride (1.0 molar) in tetrahydrofuran is then added dropwise, and the reaction is warmed to room temperature and quenched by dropwise addition of saturated aqueous ammonium chloride. The solution is diluted with methylene chloride and washed three times with water and once with brine. Drying over magnesium sulfate and removal of solvent gives a viscous oil which is triturated with ether to give the title compound.

후처리

  1. temperatureTh solution is heated
  2. temperatureat reflux for 5 hours
  3. temperaturethe reaction is warmed to room temperature
  4. customquenched by dropwise addition of saturated aqueous ammonium chloride
  5. additionThe solution is diluted with methylene chloride
  6. washwashed three times with water
  7. dry with materialDrying over magnesium sulfate and removal of solvent
  8. customgives a viscous oil which
  9. customis triturated with ether

출처 및 근거

ORD 기록
ord-d0061b22668941c1829a4bfb896d9772
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04530922

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