Tetrahydrofuran → HCID 19967702, compound

HRID 975738Notes

Reaction equation

HRID 975738 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:48]2[CH2:53][CH2:52][CH:51]([CH:54]3[CH2:59][CH2:58][CH2:57][CH2:56][C:55]3=O)[CH2:50][CH2:49]2)[CH:44]=[CH:45][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:57]1[CH2:56][CH2:55][CH:54]([CH:51]2[CH2:50][CH2:49][CH:48]([C:43]3[CH:44]=[CH:45][C:46]([F:47])=[C:41]([F:40])[CH:42]=3)[CH2:53][CH2:52]2)[CH2:59][CH2:58]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 19967698HCID 19967698, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19967702HCID 19967702, 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 (12.3 g, 27 mmols), followed by adding tetrahydrofuran (100 ml), suspending, and stirring under ice cooling till the liquid temperature reached 10° C. The reaction mixture was 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, and dropwise adding a tetrahydrofuran (50 ml) solution of (4-(3,4-difluorophenyl)cyclohexylcyclohexanone (7.3 g, 25 mmols) over 30 minutes from the dropping funnel. Further, the resulting reaction mixture was stirred for 5 hours after completion of the dropwise addition, followed by 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-(4-(3,4-difluorophenyl)cyclohexyl)cyclohexane.

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. customFurther, the resulting reaction mixture
  7. stirringwas stirred for 5 hours
  8. additionafter completion of the dropwise addition
  9. filtrationfiltering off
  10. concentrationconcentrating the filtrate under reduced pressure
  11. customisolating
  12. custompurifying the resulting pale brown oil by means of silica gel column chromatography

Sources & evidence

ORD record
ord-80ca23aa48c74831954891eaf3b7ddbc
Source dataset
uspto-grants-1997_03
Patent number
US05609791

Reaction notes

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