Tetrahydrofuran → 1-(2-(1,3-Dioxan-2-yl)ethylidene)-4-(4-cyanophenyl)cyclohexane

HRID 975734

반응식

HRID 975734 반응식
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[K+].[C:40]([C:42]1[CH:47]=[CH:46][C:45]([CH:48]2[CH2:53][CH2:52][C:51](=O)[CH2:50][CH2:49]2)=[CH:44][CH:43]=1)#[N:41]>CCOCC>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[CH2:8][CH:9]=[C:51]1[CH2:50][CH2:49][CH:48]([C:45]2[CH:46]=[CH:47][C:42]([C:40]#[N:41])=[CH:43][CH:44]=2)[CH2:53][CH2:52]1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 157899134-(4-Oxocyclohexyl)benzonitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 157899141-(2-(1,3-Dioxan-2-yl)ethylidene)-4-(4-cyanophenyl)cyclohexane수율 56%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Into a three-necked flask equipped with a dropping funnel, a three-way cock and a thermometer, was placed 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (12.2 g, 27 mmols), followed by adding tetrahydrofuran (200 ml), suspending, stirring the suspension under ice cooling till the liquid temperature reached 10° C., adding to the reaction mixture, potassium t-butoxide (30 g, 27 mmols), elevating the temperature up to room temperature under ice cooling for one hour, stirring the mixture for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(4-cyanophenyl)cyclohexanone (5.0 g, 25 mmols) from the dropping funnel over 30 minutes. The reaction mixture was stirred for 5 hours after completion of the dropwise addition, followed by adding ether (100 ml), allowing the mixture to stand, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure, and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(4-cyanophenyl)cyclohexane (4.1 g, 14 mmols).

후처리

  1. customInto a three-necked flask equipped with a dropping funnel
  2. customreached 10° C.
  3. customup to room temperature
  4. customfor one hour
  5. stirringstirring the mixture for one hour
  6. stirringThe reaction mixture was stirred for 5 hours
  7. additionafter completion of the dropwise addition
  8. filtrationfiltering off
  9. concentrationconcentrating the filtrate under reduced pressure
  10. customisolating
  11. custompurifying the resulting pale brown oil by means of silica gel column chromatography

출처 및 근거

ORD 기록
ord-7851b3b664924520ae9dc9363174e9e9
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05609791

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