Tetrahydrofuran → HCID 22915773, compound

HRID 975737Notes

Reaction equation

HRID 975737 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:52]2[CH2:57][CH2:56][C:55](=O)[CH2:54][CH2:53]2)[CH:44]=[CH:45][C:46]=1[O:47][C:48]([F:51])([F:50])[F:49]>CCOCC>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[CH2:8][CH:9]=[C:55]1[CH2:54][CH2:53][CH:52]([C:43]2[CH:44]=[CH:45][C:46]([O:47][C:48]([F:49])([F:51])[F:50])=[C:41]([F:40])[CH:42]=2)[CH2:57][CH2:56]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 21993296HCID 21993296, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22915773HCID 22915773, 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 (9.1 g, 20 mmols), followed by adding tetrahydrofuran (100 ml), suspending, stirring under ice cooling till the liquid temperature reached 10° C. The resulting reaction mixture was added potassium t-butoxide (2.2 g, 20 mmols) followed by 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-fluoro-4-trifluoromethoxyphenyl)cyclohexanone (5.5 g, 20 mmols) over 30 minutes from the dropping funnel, 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-fluoro-4-trifluoromethoxyphenyl)cyclohexane.

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 the reaction mixture 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-3d6b4dcedbe442a196abf4b41ac97d26
Source dataset
uspto-grants-1997_03
Patent number
US05609791

Reaction notes

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