Tetrahydrofuran → HCID 54480482, compound

HRID 1941035Notes

Reaction equation

HRID 1941035 reaction equation
C1COCC1.[Br-].[O:7]1[CH2:12][CH2:11][CH2:10][O:9][CH:8]1[CH2:13][CH2:14]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].O=[C:41]1[CH2:46][CH2:45][CH:44]([CH:47]2[CH2:52][CH2:51][CH:50]([CH2:53][CH2:54][C:55]3[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][CH:56]=3)[CH2:49][CH2:48]2)[CH2:43][CH2:42]1>O>[O:9]1[CH2:10][CH2:11][CH2:12][O:7][CH:8]1[CH2:13][CH2:14][CH:41]1[CH2:42][CH2:43][CH:44]([CH:47]2[CH2:48][CH2:49][CH:50]([CH2:53][CH2:54][C:55]3[CH:60]=[CH:59][C:58]([C:61]([F:62])([F:63])[F:64])=[CH:57][CH:56]=3)[CH2:51][CH2:52]2)[CH2:45][CH2:46]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 21459442HCID 21459442, compoundHCID 23665647Potassium tert-butoxideHCID 178419403HCID 178419403, compound

Product 1

HCID 54480482HCID 54480482, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

THF (70 ml) was added to 1,3-dioxan-2-ylethyltriphenylphosphinebromide (6.80 g, 14.9 mmol), followed by adding to the mixture, potassium-t-butoxide (1.68 g, 14.9 mmol) at 0° C., stirring the mixture at the same temperature for 3 hours, dropwise adding to the reaction solution, a 10 ml THF solution of the above 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethylphenyl)ethyl)cyclohexane (2.7 g, 7.7 mmol), stirring the mixture at the same temperature for one hour, further stirring at room temperature for 3 hours, adding water (50 ml) to the reaction solution, extracting the resulting product with ethyl acetate, washing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, distilling off the solvent, purifying the resulting residue according to column chromatography treatment using heptane/ethyl acetate (3/1) as a developing solvent, on silica gel, distilling off the solvent, hydrogenating the residue (3.2 g) in the presence of a catalyst of 5% Pd/C (0.15 g), in ethanol solvent, filtering off the catalyst distilling off the solvent under reduced pressure, and recrystallizing the residue from heptane/ethanol (5/1), to obtain 4-(4-(1,3-dioxan-2-ylethyl)cyclohexyl)-1-(2-(4-trifluoromethylphenyl)ethyl)cyclohexane (1.46 g, 3.23 mmol). The yield of this product from 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethylphenyl)ethyl)cyclohexane was 42%.

Workup

  1. additiondropwise adding to the reaction solution
  2. stirringfurther stirring at room temperature for 3 hours
  3. extractionextracting the resulting product with ethyl acetate
  4. washwashing the organic layer successively with a saturated, aqueous solution of sodium bicarbonate and water
  5. dry with materialdrying over magnesium sulfate
  6. distillationdistilling off the solvent
  7. custompurifying the resulting residue
  8. distillationon silica gel, distilling off the solvent
  9. filtrationin ethanol solvent, filtering off the catalyst
  10. distillationdistilling off the solvent under reduced pressure
  11. customrecrystallizing the residue from heptane/ethanol (5/1)

Sources & evidence

ORD record
ord-9369f94ea6a845798f65eeb05ef1a040
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

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