Tetrahydrofuran → HCID 22915740, compound

HRID 1376298Notes

Reaction equation

HRID 1376298 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]([F:56])([F:55])[C:42]1[CH:47]=[CH:46][C:45]([CH:48]2[CH2:53][CH2:52][C:51](=O)[CH2:50][CH2:49]2)=[CH:44][CH:43]=1>CCOCC>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[CH2:8][CH:9]=[C:51]1[CH2:50][CH2:49][CH:48]([C:45]2[CH:44]=[CH:43][C:42]([C:41]([F:40])([F:55])[F:56])=[CH:47][CH:46]=2)[CH2:53][CH2:52]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 184002174-[4-(Trifluoromethyl)phenyl]cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22915740HCID 22915740, 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 (12.2 g, 27 mmols), followed by adding tetrahydrofuran (100 ml), suspending, and stirring under ice cooling till the liquid temperature reached 10° C. The resulting reaction mixture was added potassium t-butoxide (3.0 g, 27 mmols), followed by elevating the temperature up to room temperature under ice cooling, stirring for one hour, dropwise adding a tetrahydrofuran (50 ml) solution of 4-(4-trifluoromethylphenyl) cyclohexanone (6.0 g, 25 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-(4-trifluoromethylphenyl)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. 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-8cf815e5db0f4039a32a299cc31c811a
Source dataset
uspto-grants-1997_09
Patent number
US05662830

Reaction notes

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