Ammonium Chloride → 4-(4-(4-Fluorophenyl)-3-cyclohexenyl)-1-phenyl-1-n-propyl-1-silacyclohexane

HRID 1938872

반응식

HRID 1938872 반응식
[C:1]1([Si:7]2([CH2:20][CH2:21][CH3:22])[CH2:12][CH2:11][CH:10]([CH:13]3[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Cl)=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:16]2[CH2:17][CH2:18][CH:13]([CH:10]3[CH2:11][CH2:12][Si:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([CH2:20][CH2:21][CH3:22])[CH2:8][CH2:9]3)[CH2:14][CH:15]=2)=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 110343904-(4-Phenyl-4-n-propyl-4-silacyclohexyl)cyclohexanoneHCID 178505844HCID 178505844, 화합물

생성물 1

HCID 110146944-(4-(4-Fluorophenyl)-3-cyclohexenyl)-1-phenyl-1-n-propyl-1-silacyclohexane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

31.5 g of 4-(4-phenyl-4-n-propyl-4-silacyclohexyl)cyclohexanone was dropped in 120 ml of a solution of 1.0 mole of p-fluorophenylmagnesium chloride in tetrahydrofuran at a temperature of 40° to 50° C. After agitation at 50° C. for 2 hours, the reaction mixture was poured into a saturated ammonium chloride aqueous solution, followed by extraction with benzene. 1.0 g of p-toluenesulfonic acid monohydrate was added to the benzene phase, followed by distilling off the resultant water under reflux. When the distilling of water stopped, the benzene solution was washed with a sodium hydrogencarbonate aqueous solution, dried and concentrated to obtain crude 4-(4-(4-fluorophenyl)-3-cyclohexenyl)-1-phenyl-1-n-propyl-1-silacyclohexane. This product was dissolved in 100 ml of ethanol and hydrogenated in the presence of 1.0 g of a palladium-carbon catalyst, followed by separation of the catalyst by filtration and concentration to obtain 35.0 g (yield: 88%) of 4-(4-(4-fluorophenyl)cyclohexyl)-1-phenyl-1-n-propyl-1-silacyclohexane. The results of IR analysis are shown below.

후처리

  1. extractionfollowed by extraction with benzene
  2. addition1.0 g of p-toluenesulfonic acid monohydrate was added to the benzene phase
  3. distillationby distilling off the resultant water
  4. temperatureunder reflux
  5. distillationWhen the distilling of water
  6. washthe benzene solution was washed with a sodium hydrogencarbonate aqueous solution
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a37cfc918087414ab4f63756e707615a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05693841

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