Triphenylphosphine → 1-(4-propylphenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene

HRID 1609432노트

반응식

HRID 1609432 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1)[CH2:21][CH3:22].C(C1C=CC(CCO)=CC=1)CC.CC(C)([O-])C.[K+].[CH2:50]([CH:55]1[CH2:60][CH2:59][CH:58]([CH:61]2[CH2:66][CH2:65][CH:64]([CH2:67][CH:68]=O)[CH2:63][CH2:62]2)[CH2:57][CH2:56]1)[CH2:51][CH2:52][CH2:53][CH3:54]>C1COCC1.CCOCC.C1(C)C(C)=CC=CC=1>[CH2:20]([C:23]1[CH:31]=[CH:30][C:26](/[CH:27]=[CH:28]\[CH2:68][CH2:67][CH:64]2[CH2:65][CH2:66][CH:61]([CH:58]3[CH2:57][CH2:56][CH:55]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:60][CH2:59]3)[CH2:62][CH2:63]2)=[CH:25][CH:24]=1)[CH2:21][CH3:22]

참가 물질

9

반응물 5

HCID 11776TriphenylphosphineHCID 27604762-(4-Propylphenyl)ethanolHCID 111404394-(4-Pentylcyclohexyl)cyclohexylacetoaldehydeHCID 200811661-(2-Bromoethyl)-4-propylbenzeneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 867485931-(4-propylphenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene수율 50%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 7237O-Xylene용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Into a flask, were placed triphenylphosphine (2.3 g, 8.8 mmol) and 4-propylphenethylbromide (2.0 g, 8.8 mmol) prepared from 4-propylphenethyl alcohol, followed by adding and dissolving xylene (10 ml), heating under reflux for 10 hours, filtering off white crystals of 4-propylphenethyltriphenylphosphoniumbromide deposited after the completion of reaction, drying the obtained white crystals (4.3 g, 8.8 mmol), dissolving the white crystals in THF (10 ml), stirring under ice cooling, adding potassium-t-butoxide (984 mg, 8.8 mmol) to the reaction solution slowly, stirring the solution at room temperature for 2 hours after the completion of dropping, adding a THF solution of 4-(4-pentylcyclohexyl)cyclohexylacetoaldehyde (2.45 g, 8.8 mmol), further stirring for 5 hours, adding ether after completion of reaction, filtering off white solid deposited, concentrating the filtrate under reduced pressure, and purifying the obtained brown oil by means of silica gel column chromatography, to obtain a mixture (1.8 g, 4.4 mmol) of 1-(4-propylphenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene and its E-isomer.

후처리

  1. customInto a flask, were placed
  2. additionby adding
  3. temperatureheating
  4. temperatureunder reflux for 10 hours
  5. filtrationfiltering off white crystals of 4-propylphenethyltriphenylphosphoniumbromide
  6. customafter the completion of reaction
  7. stirringstirring the solution at room temperature for 2 hours after the completion
  8. stirringfurther stirring for 5 hours
  9. customafter completion of reaction
  10. filtrationfiltering off white solid
  11. concentrationconcentrating the filtrate under reduced pressure
  12. custompurifying the obtained brown oil by means of silica gel column chromatography

출처 및 근거

ORD 기록
ord-31648d9c3f6b4a66a6cece36bad7101d
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05401434

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