Tetrahydrofuran → 1-(2-(1,3-Dioxan-2-yl)ethylidene)-4-(3,4,5-trifluorophenyl)cyclohexane

HRID 1376297Notes

Reaction equation

HRID 1376297 reaction equation
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CC(C)([O-])C.[K+].[F:40][C:41]1[CH:42]=[C:43]([CH:49]2[CH2:54][CH2:53][C:52](=O)[CH2:51][CH2:50]2)[CH:44]=[C:45]([F:48])[C:46]=1[F:47]>CCOCC>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[CH2:8][CH:9]=[C:52]1[CH2:51][CH2:50][CH:49]([C:43]2[CH:44]=[C:45]([F:48])[C:46]([F:47])=[C:41]([F:40])[CH:42]=2)[CH2:54][CH2:53]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 219932844-(3,4,5-Trifluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 229157561-(2-(1,3-Dioxan-2-yl)ethylidene)-4-(3,4,5-trifluorophenyl)cyclohexane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a three-necked flask equipped with a dropping fumel, a three-way cock and a thermometer was placed 2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (12.2 g, 27 mole), followed by adding tetrahydrofuran (200 ml), suspending it, stirring under ice cooling till the liquid temperature reached 10° C., adding potassium t-butoxide (3.0 g, 27 mmols) to the reaction mixture, further elevating the temperature up to room temperature under ice cooling for one hour, stirring for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(3,4,5-trifluorophenyl)cyclohexanone (5.7 g, 25 mmols) from the dropping funnel over 30 minutes, further stirring the reaction mixture for 5 hours after completion of the dropwise addition, adding ether (100 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-(3,4,5-trifluorophenyl)cyclohexane.

Workup

  1. customInto a three-necked flask equipped with a dropping fumel
  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 oil by means of silica gel column chromatography

Sources & evidence

ORD record
ord-52dbbd7aecd8482cb8c168945f1988d3
Source dataset
uspto-grants-1997_09
Patent number
US05662830

Reaction notes

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