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

HRID 1609433Notes

Reaction equation

HRID 1609433 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f620ef707b3340d28e49755e170121b4
Source dataset
uspto-grants-1995_03
Patent number
US05401434

Reaction notes

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