Water → HCID 178447944, compound

HRID 641098Notes

Reaction equation

HRID 641098 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1(O)[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C@H]2CC[C@H](CCC)CC2)[CH2:14][CH2:13]1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33](S(O)(=O)=O)=[CH:32][CH:31]=1.O.[C:42]1(C)C=CC=C[CH:43]=1>>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH2:17][CH2:16][CH:15]([CH:18]([C@H:33]2[CH2:34][CH2:35][C@H:30]([CH2:40][CH2:42][CH3:43])[CH2:31][CH2:32]2)[CH3:19])[CH2:14][CH:13]=1

Participants

5

Reactant 4

HCID 962Water2×HCID 1140Toluene2×HCID 6101p-Toluenesulfonic acidHCID 178447951HCID 178447951, compound

Product 1

HCID 178447944HCID 178447944, compound

Procedure

16.4 g of the compound (8), 0.2 g of p-toluenesulfonic acid and 80 mL of toluene were mixed, and the mixture was refluxed under heating for 2 hours while water distilled out was removed. After cooling the resulting reaction mixture to 25° C., 200 mL of water and 200 mL of toluene were added to and mixed with the reaction mixture, which was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=4/1 by volume) as eluent, and then further purified by recrystallization from a mixed solvent of heptane and ethanol (heptane/ethanol=2/1 by volume) to obtain 6.2 g of 2-chloro-4-ethoxy-3-fluoro-1-(4-(2-(trans-4-propylcyclohexyl)-2-ethyl)-cyclohexa-1-enyl)benzene (No. 103). The yield based on the compound (7) was 42.4%.

Workup

  1. temperaturethe mixture was refluxed
  2. distillationdistilled out
  3. customwas removed
  4. temperatureAfter cooling
  5. customthe resulting reaction mixture to 25° C.
  6. additionmixed with the reaction mixture, which
  7. customwas separated into an organic layer
  8. extractionextraction to the organic layer
  9. washwashed with a 2N sodium hydroxide aqueous solution
  10. dry with materialby drying over anhydrous magnesium sulfate
  11. distillationThereafter, the solvent was distilled off under reduced pressure
  12. customto obtain a residue
  13. customThe resulting residue was purified by silica gel column chromatography
  14. customfurther purified by recrystallization from a mixed solvent of heptane and ethanol (heptane/ethanol=2/1 by volume)

Sources & evidence

ORD record
ord-2538db83a4624407b45d8eddf569e364
Source dataset
uspto-grants-2010_04
Patent number
US07695777B2

Reaction notes

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