Tetrahydrofuran → 4-(4-Propylcyclohexyl)cyclohexane

HRID 975742

Reaction equation

HRID 975742 reaction equation
[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[K+].[CH2:32]([CH:35]1[CH2:40][CH2:39][CH:38]([CH:41]2[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]2)[CH2:37][CH2:36]1)[CH2:33][CH3:34]>CCOCC>[CH2:32]([CH:35]1[CH2:40][CH2:39][CH:38]([CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:37][CH2:36]1)[CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 517696Phosphine, triphenyl-, hydrobromideHCID 4354185[1,1'-Bicyclohexyl]-4-one,4'-propyl-,HCID 23665647Potassium tert-butoxide

Product 1

HCID 178840974-(4-Propylcyclohexyl)cyclohexaneYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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)ethyl)triphenylphosphonium bromide (12.3 g, 27 mmols), followed by adding tetrahydrofuran (50 ml), suspending, stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture is added potassium t-butoxide (3.0 g, 27 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (10 ml) solution of 4-(4-propylcyclohexyl)cyclohexanone (15.6 g, 25 mmols) over 30 minutes from the dropping funnel, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (50 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure, isolating and purifying the resulting pale brown oily substance by means of silica gel column chromatography and recrystallizing from ethanol, to obtain 1-(2-(1,3-dioxan)-2-yl)ethylidene)-4-(4-propylcyclohexyl)cyclohexane (4.5 g, 14 mmols).

Workup

  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 for one hour
  6. stirringfurther stirring the reaction mixture 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 oily substance by means of silica gel column chromatography
  12. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-b6001f375b1c4dde9bc2c80ccc1b1963
Source dataset
uspto-grants-1997_03
Patent number
US05609791

Linked notes

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