Tetrahydrofuran → HCID 54564561, compound

HRID 1941040Notes

Reaction equation

HRID 1941040 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]([O:61][C:62]([F:65])([F:64])[F:63])=[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:56]=[CH:57][C:58]([O:61][C:62]([F:63])([F:64])[F:65])=[CH:59][CH:60]=3)[CH2:51][CH2:52]2)[CH2:45][CH2:46]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 21459475HCID 21459475, compoundHCID 23665647Potassium tert-butoxideHCID 178419403HCID 178419403, compound

Product 1

HCID 54564561HCID 54564561, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

THF (100 ml) was added to 1,3-dioxan-2-ylethyltriphenylphosphinebromide (10.0 g, 21.9 mmol), followed by adding thereto potassium-t-butoxide (2.46 g, 21.9 mmol), stirring the mixture at the same temperature for 3 hours, dropwise adding to the reaction solution, a 20 ml THF solution of the above 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexane (5.7 g, 15.6 mmol), stirring the mixture at the same temperature for one hour, stirring for 3 hours at room temperature, adding water (100 ml) to the reaction solution, extracting the 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 (5.1 g) in the presence of a catalyst of 5% Pd/C (0.30 g) in an ethanol solution, 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-trifluoromethoxyphenyl)ethyl)cyclohexane (3.25 g, 6.94 mmol). The yield of this product from 4-(4-oxocyclohexyl)-1-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexane was 44.5%.

Workup

  1. additionby adding
  2. additiondropwise adding to the reaction solution
  3. extractionextracting the 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. filtrationfiltering 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-6ca5bafd945547a1ae0b9b8d99451dba
Source dataset
uspto-grants-1997_12
Patent number
US05702641

Reaction notes

Loading…