Tetrahydrofuran → HCID 86748971, compound

HRID 2399600Notes

Reaction equation

HRID 2399600 reaction equation
[Br-].O1CCCOC1CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[CH2:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51]([CH:54]3[CH2:59][CH2:58][CH2:57][CH2:56][C:55]3=O)=[CH:50][CH:49]=2)=[CH:44][CH:43]=1)[CH2:40][CH3:41]>CCOCC>[CH2:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:49]=[CH:50][C:51]([CH:54]3[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]3)=[CH:52][CH:53]=2)=[CH:44][CH:43]=1)[CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 45749132-Methylpropan-2-olateHCID 22915889HCID 22915889, compound

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 temperature reached 10° C. The resulting reaction mixture is added pottasium 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 (100ml) 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 reduce pressure and isolating and purifying the resulting pale brown oil by means of silica gel column chromatography, to obtain 1-(2-(2,3-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
  12. customisolating
  13. custompurifying the resulting pale brown oil by means of silica gel column chromatography

Sources & evidence

ORD record
ord-98039f79aeb3466da87d83d2f06a6fd5
Source dataset
uspto-grants-1995_09
Patent number
US05449810

Reaction notes

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