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

HRID 1609432ノート

反応式

HRID 1609432 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 7237O-Xylene溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31648d9c3f6b4a66a6cece36bad7101d
出典データセット
uspto-grants-1995_03
特許番号
US05401434

反応ノート

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