Tetrahydrofuran → HCID 86748971, compound

HRID 1376300Notes

Reaction equation

HRID 1376300 reaction equation
[Br-].O1CCCOC1CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[K+].[CH2:40]([C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([CH:55]3[CH2:60][CH2:59][CH2:58][CH2:57][C:56]3=O)=[CH:51][CH:50]=2)=[CH:45][CH:44]=1)[CH2:41][CH3:42]>CCOCC>[CH2:40]([C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:50]=[CH:51][C:52]([CH:55]3[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]3)=[CH:53][CH:54]=2)=[CH:45][CH:44]=1)[CH2:41][CH3:42]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 22915889HCID 22915889, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86748971HCID 86748971, compound

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)ethyltriphenylphosphonium bromide (22.9 g, 50 mmols), followed by adding tetrahydrofuran (100 ml), suspending, stirring the suspension under ice cooling till the liquid temperautre reached 10° C. The resulting reaction mixture is added potassium t-butoxide (5.6 g, 50 mmols), followed by elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (100 ml) solution of (4-(4-propylphenyl)phenyl)cyclohexanone (14.0 g, 48 mmols) over 30 minutes from the dropping funnel, further stirring the reaction liquid for 5 hours after completion of the dropwise addition, adding ether (200 ml), allowing to stand for one hour, filtering off deposited insoluble substance, concentrating the filtrate under reduced pressure and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(1,3-dioxan-2-yl)ethylidene)-4-(4-(4-propylphenyl)phenylcyclohexane.

Workup

  1. customInto a three-necked flask equipped with a dropping funnel
  2. customreached 10° C
  3. customThe resulting reaction mixture
  4. customup to room temperature
  5. customfor one hour
  6. stirringstirring for one hour
  7. stirringfurther stirring
  8. customthe reaction liquid for 5 hours
  9. additionafter completion of the dropwise addition
  10. filtrationfiltering off
  11. concentrationconcentrating the filtrate under reduced pressure
  12. customisolating
  13. custompurifying the resulting pale brown oil by means of silica gel column chromatography

Sources & evidence

ORD record
ord-41fc16c337c24790b26ea80cc98d22e4
Source dataset
uspto-grants-1997_09
Patent number
US05662830

Reaction notes

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