Diethyl Ether → 1-(4-fluorophenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene

HRID 1609433노트

반응식

HRID 1609433 반응식
[Br-].[F:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[CH2:36]([CH:41]1[CH2:46][CH2:45][CH:44]([CH:47]2[CH2:52][CH2:51][CH:50]([CH2:53][CH:54]=O)[CH2:49][CH2:48]2)[CH2:43][CH2:42]1)[CH2:37][CH2:38][CH2:39][CH3:40].CCOCC>C1COCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:7]=[CH:8]\[CH2:54][CH2:53][CH:50]2[CH2:51][CH2:52][CH:47]([CH:44]3[CH2:43][CH2:42][CH:41]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:46][CH2:45]3)[CH2:48][CH2:49]2)=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 111404394-(4-Pentylcyclohexyl)cyclohexylacetoaldehydeHCID 223867454-Fluorophenethyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 867485941-(4-fluorophenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene수율 57.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-fluorophenethyltriphenylphosphoniumbromide (4.2 g, 9 mmol) was dried and then dissolved in THF (10 ml), followed by stirring under ice cooling, adding potassium-t-butoxide (1.0 g, 9 mmol) slowly to the obtained reaction solution, stirring at room temperature for 2 hours after the completion of dropping, adding a THF (50 ml) solution of 4-(4-pentylcyclohexyl)-cyclohexylacetoaldehyde (2.7 g, 9.7 mmol) and further stirring for 5 hours, adding ether after the completion of reaction, filtering off the obtained white crystals deposited, concentrating the filtrate under reduced pressure, and purifying the obtained brown oil by means of silica gel column chromatography, to obtain a mixture (2.0 g, 5.2 mmol) of 1-(4-fluorophenyl)-4-(4-(4-pentylcyclohexyl)cyclohexyl)-2Z-butene with its E-isomer.

후처리

  1. customslowly to the obtained reaction solution
  2. stirringstirring at room temperature for 2 hours after the completion
  3. stirringfurther stirring for 5 hours
  4. customafter the completion of reaction
  5. filtrationfiltering off the obtained white crystals
  6. concentrationconcentrating the filtrate under reduced pressure
  7. custompurifying the obtained brown oil by means of silica gel column chromatography

출처 및 근거

ORD 기록
ord-f620ef707b3340d28e49755e170121b4
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05401434

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